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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2500 Lee Rd #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: 6.04% Traditional cash on cash: 3.58% Airbnb Rental Income: $2559 Traditional Rental Income: $1477 Airbnb ROI: 6.04% Traditional ROI: 3.58%
1695 Lee Rd #E103 Winter Park, FL One or more photo(s) has been virtually staged. One or more photo(s) has been virtually st...	2 beds \| 1 baths \| 881 sq.ft.	$134,900	Airbnb cash on cash: 7.67% Traditional cash on cash: 7.52% Airbnb Rental Income: $2559 Traditional Rental Income: $1924 Airbnb ROI: 7.67% Traditional ROI: 7.52%
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%
151 N Orlando Ave #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: 2.79% Traditional cash on cash: 3.27% Airbnb Rental Income: $2559 Traditional Rental Income: $2075 Airbnb ROI: 2.79% Traditional ROI: 3.27%
1695 LEE ROAD #E204 Winter Park, FL Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a f...	2 beds \| 1 baths \| 881 sq.ft.	$114,000	Airbnb cash on cash: 9.29% Traditional cash on cash: 9.35% Airbnb Rental Income: $2559 Traditional Rental Income: $1950 Airbnb ROI: 9.29% Traditional ROI: 9.35%
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%
630 Killarney Bay Ct #3 Winter Park, FL Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedro...	2 beds \| 2 baths \| 1,428 sq.ft.	$475,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 1.95% Airbnb Rental Income: $2559 Traditional Rental Income: $2514 Airbnb ROI: 0.67% 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: 0.53% Traditional cash on cash: 2.83% Airbnb Rental Income: $2443 Traditional Rental Income: $2954 Airbnb ROI: 0.53% Traditional ROI: 2.83%
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%
1695 LEE ROAD #E116 Winter Park, FL Under contract-accepting backup offers. Located in the heart of Winter Park, this 3-bedroo...	3 beds \| 2 baths \| 1,149 sq.ft.	$110,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.05% Airbnb Rental Income: $2443 Traditional Rental Income: $1750 Airbnb ROI: 6.96% Traditional ROI: 6.05%
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: 3.92% Traditional cash on cash: 4.16% Airbnb Rental Income: $2559 Traditional Rental Income: $2029 Airbnb ROI: 3.92% 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: 4.73% Traditional cash on cash: 7.59% Airbnb Rental Income: $1806 Traditional Rental Income: $1655 Airbnb ROI: 4.73% Traditional ROI: 7.59%
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%
7336 Forest Hill Ct #240 Winter Park, FL Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for yo...	2 beds \| 1 baths \| 990 sq.ft.	$169,900	Airbnb cash on cash: 5.66% Traditional cash on cash: 6.19% Airbnb Rental Income: $2559 Traditional Rental Income: $2029 Airbnb ROI: 5.66% Traditional ROI: 6.19%
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%
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%
3019 Antique Oaks Cir #124 Winter Park, FL What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED...	1 beds \| 1 baths \| 749 sq.ft.	$142,500	Airbnb cash on cash: 4.04% Traditional cash on cash: 7.23% Airbnb Rental Income: $1806 Traditional Rental Income: $1758 Airbnb ROI: 4.04% Traditional ROI: 7.23%
2383 Sun Valley Cir #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.	$245,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 3.07% Airbnb Rental Income: $2559 Traditional Rental Income: $1847 Airbnb ROI: 3.48% Traditional ROI: 3.07%
311 Scottsdale Sq #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.	$109,500	Airbnb cash on cash: -12.58% Traditional cash on cash: -10.35% Airbnb Rental Income: $1806 Traditional Rental Income: $1552 Airbnb ROI: -12.58% Traditional ROI: -10.35%
205 Lewfield Cir #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: 6.28% Traditional cash on cash: 5.09% Airbnb Rental Income: $2559 Traditional Rental Income: $1737 Airbnb ROI: 6.28% Traditional ROI: 5.09%
7300 Daniel Webster Dr #M7 Winter Park, FL Welcome home to this stunningly updated two-story condo that perfectly combines modern ele...	2 beds \| 2 baths \| 1,108 sq.ft.	$159,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 6.28% Airbnb Rental Income: $2559 Traditional Rental Income: $1914 Airbnb ROI: 6.47% Traditional ROI: 6.28%
3027 Aaron Burr Ave #L1 Winter Park, FL Step into this beautifully renovated two-story condo offering the perfect blend of modern ...	2 beds \| 2 baths \| 1,090 sq.ft.	$159,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 6.23% Airbnb Rental Income: $2559 Traditional Rental Income: $1907 Airbnb ROI: 6.47% Traditional ROI: 6.23%
5143 Lazy Oaks Dr #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.	$275,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 3.64% Airbnb Rental Income: $2559 Traditional Rental Income: $1668 Airbnb ROI: 4.7% Traditional ROI: 3.64%
2317 Sun Valley Cir #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.	$249,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.42% Airbnb Rental Income: $2559 Traditional Rental Income: $1846 Airbnb ROI: 3.82% 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: 4.74% Traditional cash on cash: 5.34% Airbnb Rental Income: $2559 Traditional Rental Income: $2054 Airbnb ROI: 4.74% Traditional ROI: 5.34%
2503 Tahoe Cir #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: 6.63% Traditional cash on cash: 5.56% Airbnb Rental Income: $2559 Traditional Rental Income: $1692 Airbnb ROI: 6.63% Traditional ROI: 5.56%
4798 Tangerine Ave #4798 Winter Park, FL Welcome to this charming and well-maintained condominium located in the desirable Winter P...	2 beds \| 2 baths \| 1,058 sq.ft.	$180,000	Airbnb cash on cash: 9.59% Traditional cash on cash: 7.27% Airbnb Rental Income: $2559 Traditional Rental Income: $1547 Airbnb ROI: 9.59% Traditional ROI: 7.27%
3217 OAK LAWN PLACE #211 Winter Park, FL Rare corner unit opportunity â this 3-bedroom, 2-bath home sits on the upper level of th...	3 beds \| 2 baths \| 1,117 sq.ft.	$172,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 7.59% Airbnb Rental Income: $2443 Traditional Rental Income: $2239 Airbnb ROI: 5.2% Traditional ROI: 7.59%
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: 3.45% Traditional cash on cash: 4.51% Airbnb Rental Income: $2443 Traditional Rental Income: $2116 Airbnb ROI: 3.45% 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: 5.51% Traditional cash on cash: 5.86% Airbnb Rental Income: $2559 Traditional Rental Income: $2012 Airbnb ROI: 5.51% 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: 4.4% Traditional cash on cash: 4.22% Airbnb Rental Income: $2559 Traditional Rental Income: $1906 Airbnb ROI: 4.4% Traditional ROI: 4.22%

Your search for investment property begins and ends here

Condos for Sale in Winter Park, FL

2500 Lee Rd #220

Winter Park, FL

2 beds | 1 baths | 851 sq.ft.

$199,900

Airbnb cash on cash: 6.04%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $2559

Traditional Rental Income: $1477

Airbnb ROI: 6.04%

Traditional ROI: 3.58%

1695 Lee Rd #E103

Winter Park, FL

2 beds | 1 baths | 881 sq.ft.

$134,900

Airbnb cash on cash: 7.67%

Traditional cash on cash: 7.52%

Airbnb Rental Income: $2559

Traditional Rental Income: $1924

Airbnb ROI: 7.67%

Traditional ROI: 7.52%

2500 Lee Rd #208

Winter Park, FL

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%

151 N Orlando Ave #115

Winter Park, FL

2 beds | 1 baths | 710 sq.ft.

$290,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $2559

Traditional Rental Income: $2075

Airbnb ROI: 2.79%

Traditional ROI: 3.27%

1695 LEE ROAD #E204

Winter Park, FL

2 beds | 1 baths | 881 sq.ft.

$114,000

Airbnb cash on cash: 9.29%

Traditional cash on cash: 9.35%

Airbnb Rental Income: $2559

Traditional Rental Income: $1950

Airbnb ROI: 9.29%

Traditional ROI: 9.35%

1809 Hammerlin Ave

Winter Park, FL

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%

630 Killarney Bay Ct #3

Winter Park, FL

2 beds | 2 baths | 1,428 sq.ft.

$475,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $2559

Traditional Rental Income: $2514

Airbnb ROI: 0.67%

Traditional ROI: 1.95%

1807 Hammerlin Ave #G

Winter Park, FL

3 beds | 2 baths | 1,818 sq.ft.

$515,000

Airbnb cash on cash: 0.53%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $2443

Traditional Rental Income: $2954

Airbnb ROI: 0.53%