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.

Condos for Sale in Winter Park, FL

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

Showing 31 Condo 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
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%
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%
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%
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%
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%
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%
630 KILLARNEY BAY COURT #3 Winter Park, FL Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedro...	2 beds \| 3 baths \| 1,428 sq.ft.	$475,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.95% Airbnb Rental Income: $3260 Traditional Rental Income: $2514 Airbnb ROI: 1.99% Traditional ROI: 1.95%
1807 Hammerlin Ave #G Winter Park, FL Virtually Staged. Price Improvement Welcome home to this beautifully updated two-s...	3 beds \| 2 baths \| 1,818 sq.ft.	$515,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.83% Airbnb Rental Income: $4337 Traditional Rental Income: $2954 Airbnb ROI: 3.8% Traditional ROI: 2.83%
1600 ALABAMA DRIVE #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: 0.76% Traditional cash on cash: 0.78% Airbnb Rental Income: $3260 Traditional Rental Income: $2554 Airbnb ROI: 0.76% Traditional ROI: 0.78%
851 MILES AVENUE #13 Winter Park, FL Under contract-accepting backup offers. Welcome to 851 Miles Ave #13, a beautifully renova...	2 beds \| 1 baths \| 808 sq.ft.	$209,999	Airbnb cash on cash: 7.99% Traditional cash on cash: 5.31% Airbnb Rental Income: $3260 Traditional Rental Income: $1995 Airbnb ROI: 7.99% Traditional ROI: 5.31%
340 KILLARNEY BAY COURT #4-4 Winter Park, FL Under contract-accepting backup offers. Welcome to 340 Killarney Bay, a beautifully mainta...	2 beds \| 3 baths \| 1,428 sq.ft.	$379,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 4.16% Airbnb Rental Income: $3260 Traditional Rental Income: $2029 Airbnb ROI: 5.56% Traditional ROI: 4.16%
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: 8.99% Traditional cash on cash: 7.59% Airbnb Rental Income: $2412 Traditional Rental Income: $1655 Airbnb ROI: 8.99% Traditional ROI: 7.59%
2918 ANTIQUE OAKS CIRCLE #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: 8.73% Traditional cash on cash: 5.4% Airbnb Rental Income: $3260 Traditional Rental Income: $1930 Airbnb ROI: 8.73% Traditional ROI: 5.4%
7336 FOREST HILL COURT #240 Winter Park, FL Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for yo...	2 beds \| 2 baths \| 990 sq.ft.	$169,900	Airbnb cash on cash: 9.27% Traditional cash on cash: 6.19% Airbnb Rental Income: $3260 Traditional Rental Income: $2029 Airbnb ROI: 9.27% Traditional ROI: 6.19%
189 LEWFIELD CIRCLE #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: 6.87% Traditional cash on cash: 5.43% Airbnb Rental Income: $2412 Traditional Rental Income: $1609 Airbnb ROI: 6.87% Traditional ROI: 5.43%
3019 ANTIQUE OAKS CIRCLE #124 Winter Park, FL What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED...	1 beds \| 1 baths \| 749 sq.ft.	$144,500	Airbnb cash on cash: 7.69% Traditional cash on cash: 7.23% Airbnb Rental Income: $2412 Traditional Rental Income: $1758 Airbnb ROI: 7.69% Traditional ROI: 7.23%
2383 SUN VALLEY CIRCLE #2383 Winter Park, FL Nestled in a peaceful setting within the serene Cedarwood Village community, this charming...	2 beds \| 2 baths \| 1,295 sq.ft.	$250,000	Airbnb cash on cash: 5.95% Traditional cash on cash: 3.07% Airbnb Rental Income: $3260 Traditional Rental Income: $1847 Airbnb ROI: 5.95% Traditional ROI: 3.07%
311 SCOTTSDALE SQUARE #311 Winter Park, FL This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a re...	1 beds \| 1 baths \| 785 sq.ft.	$109,900	Airbnb cash on cash: -7.79% Traditional cash on cash: -10.32% Airbnb Rental Income: $2412 Traditional Rental Income: $1552 Airbnb ROI: -7.79% Traditional ROI: -10.32%
205 LEWFIELD CIRCLE #205 Winter Park, FL MOTIVATED SELLER! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, ...	2 beds \| 2 baths \| 927 sq.ft.	$182,900	Airbnb cash on cash: 9.64% Traditional cash on cash: 5.09% Airbnb Rental Income: $3260 Traditional Rental Income: $1737 Airbnb ROI: 9.64% Traditional ROI: 5.09%
5143 LAZY OAKS DRIVE #5143 Winter Park, FL Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the ...	2 beds \| 2 baths \| 1,008 sq.ft.	$280,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 3.56% Airbnb Rental Income: $3260 Traditional Rental Income: $1668 Airbnb ROI: 6.82% Traditional ROI: 3.56%
2317 SUN VALLEY CIRCLE #2317 Winter Park, FL Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence ne...	2 beds \| 2 baths \| 1,295 sq.ft.	$259,000	Airbnb cash on cash: 6.21% Traditional cash on cash: 3.42% Airbnb Rental Income: $3260 Traditional Rental Income: $1846 Airbnb ROI: 6.21% Traditional ROI: 3.42%
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: 7.9% Traditional cash on cash: 5.34% Airbnb Rental Income: $3260 Traditional Rental Income: $2054 Airbnb ROI: 7.9% Traditional ROI: 5.34%
2503 TAHOE CIRCLE #2503 Winter Park, FL This charming one story condo is located in the desirable Cedarwood Village. This unique h...	2 beds \| 2 baths \| 1,173 sq.ft.	$250,000	Airbnb cash on cash: 9.1% Traditional cash on cash: 5.56% Airbnb Rental Income: $3260 Traditional Rental Income: $1692 Airbnb ROI: 9.1% Traditional ROI: 5.56%
200 SAINT ANDREWS BLVD #3206 Winter Park, FL Welcome to Four Seasons â Where Winter Park Living Meets Modern ConvenienceThis shar...	2 beds \| 2 baths \| 1,219 sq.ft.	$230,000	Airbnb cash on cash: 9.25% Traditional cash on cash: 5.65% Airbnb Rental Income: $3260 Traditional Rental Income: $1743 Airbnb ROI: 9.25% Traditional ROI: 5.65%
3037 ANTIQUE OAKS CIRCLE #156 Winter Park, FL Cute as a button and move-in ready! This charming top floor 1-bedroom, 1-bath condo offers...	1 beds \| 1 baths \| 749 sq.ft.	$154,900	Airbnb cash on cash: 9.36% Traditional cash on cash: 6.21% Airbnb Rental Income: $2412 Traditional Rental Income: $1354 Airbnb ROI: 9.36% Traditional ROI: 6.21%
256 LEWFIELD CIRCLE #256 Winter Park, FL This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready fo...	2 beds \| 2 baths \| 927 sq.ft.	$184,900	Airbnb cash on cash: 8.88% Traditional cash on cash: 5.13% Airbnb Rental Income: $3260 Traditional Rental Income: $1868 Airbnb ROI: 8.88% Traditional ROI: 5.13%
2384 SUN VALLEY CIRCLE Winter Park, FL Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit...	3 beds \| 2 baths \| 1,311 sq.ft.	$269,900	Airbnb cash on cash: 9.66% Traditional cash on cash: 4.51% Airbnb Rental Income: $4337 Traditional Rental Income: $2116 Airbnb ROI: 9.66% Traditional ROI: 4.51%
4858 TANGERINE AVENUE #4858 Winter Park, FL Under contract-accepting backup offers. Charming Updated Home in Prime Winter Park Locatio...	2 beds \| 2 baths \| 1,058 sq.ft.	$209,900	Airbnb cash on cash: 8.45% Traditional cash on cash: 5.86% Airbnb Rental Income: $3260 Traditional Rental Income: $2012 Airbnb ROI: 8.45% Traditional ROI: 5.86%
200 SAINT ANDREWS BOULEVARD #2901 Winter Park, FL Under contract-accepting backup offers. Welcome to this spacious and well-maintained 2 sto...	2 beds \| 2 baths \| 1,266 sq.ft.	$225,000	Airbnb cash on cash: 7.14% Traditional cash on cash: 4.22% Airbnb Rental Income: $3260 Traditional Rental Income: $1906 Airbnb ROI: 7.14% Traditional ROI: 4.22%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, FL

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%

151 NORTH ORLANDO AVENUE #142

Winter Park, FL

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%

2500 LEE ROAD #208

Winter Park, FL

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

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%

151 N ORLANDO AVENUE #115

Winter Park, FL

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%

2500 LEE ROAD #222

Winter Park, FL

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%

1809 Hammerlin Ave

Winter Park, FL

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%