Airbnb Properties for Sale in Winter Park, FL

Looking for a vacation rental investment in Winter Park, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Park, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb Condo 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 38 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
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.	$335,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 3.55% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.49% Traditional ROI: 3.55%
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.	$180,000	Airbnb cash on cash: 9.58% Traditional cash on cash: 7.87% Airbnb Rental Income: $3260 Traditional Rental Income: $2235 Airbnb ROI: 9.58% Traditional ROI: 7.87%
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%
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%
851 MILES AVENUE #13 Winter Park, FL Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor c...	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%
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%
1809 Hammerlin Ave Winter Park, FL 1809 Hammerlin Ave, Winter Park, FL 32789 \| Condo/Coop	3 beds \| 2 baths \| 1,818 sq.ft.	$585,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 1.92% Airbnb Rental Income: $4337 Traditional Rental Income: $2615 Airbnb ROI: 3.4% Traditional ROI: 1.92%
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.	$495,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.84% Airbnb Rental Income: $3260 Traditional Rental Income: $2514 Airbnb ROI: 1.87% Traditional ROI: 1.84%
1807 HAMMERLIN AVENUE #G Winter Park, FL Welcome home to this beautifully updated two-story end-unit, ideally located just steps fr...	3 beds \| 3 baths \| 1,818 sq.ft.	$580,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.4% Airbnb Rental Income: $4337 Traditional Rental Income: $2954 Airbnb ROI: 3.27% Traditional ROI: 2.4%
2500 LEE ROAD #243 Winter Park, FL Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community ...	1 beds \| 1 baths \| 645 sq.ft.	$145,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.94% Airbnb Rental Income: $2412 Traditional Rental Income: $1512 Airbnb ROI: 8.17% Traditional ROI: 5.94%
311 E MORSE BOULEVARD #6-3 Winter Park, FL Under contract-accepting backup offers. Discover your new downtown Winter Park ground-floo...	1 beds \| 1 baths \| 570 sq.ft.	$315,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.01% Airbnb Rental Income: $2412 Traditional Rental Income: $1704 Airbnb ROI: 0.39% Traditional ROI: -0.01%
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%
144 LEWFIELD CIRCLE #144 Winter Park, FL LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, f...	1 beds \| 1 baths \| 678 sq.ft.	$140,000	Airbnb cash on cash: 8.45% Traditional cash on cash: 6.67% Airbnb Rental Income: $2412 Traditional Rental Income: $1582 Airbnb ROI: 8.45% Traditional ROI: 6.67%
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 Price Reduction! READY TO BE SOLD! Accepting great offers. Welcome home! NEWLY RENOVATED B...	1 beds \| 1 baths \| 749 sq.ft.	$149,000	Airbnb cash on cash: 7.43% Traditional cash on cash: 6.99% Airbnb Rental Income: $2412 Traditional Rental Income: $1758 Airbnb ROI: 7.43% Traditional ROI: 6.99%
126 SCOTTSDALE SQUARE #126 Winter Park, FL Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Convenientl...	2 beds \| 2 baths \| 1,085 sq.ft.	$150,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 3.34% Airbnb Rental Income: $3260 Traditional Rental Income: $1928 Airbnb ROI: 7.52% Traditional ROI: 3.34%
296 LEWFIELD CIRCLE Winter Park, FL 1 bed, 1 bath condo in Winter Park	1 beds \| 1 baths \| 678 sq.ft.	$154,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.72% Airbnb Rental Income: $2412 Traditional Rental Income: $1563 Airbnb ROI: 7.47% Traditional ROI: 5.72%
225 LEWFIELD CIRCLE #225 Winter Park, FL One or more photo(s) has been virtually staged. **This property qualifies for a closing co...	2 beds \| 2 baths \| 953 sq.ft.	$220,000	Airbnb cash on cash: 7.74% Traditional cash on cash: 4.5% Airbnb Rental Income: $3260 Traditional Rental Income: $1852 Airbnb ROI: 7.74% Traditional ROI: 4.5%
7707 COUNTRY PLACE #4 Winter Park, FL Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. ...	2 beds \| 2 baths \| 1,068 sq.ft.	$250,000	Airbnb cash on cash: 7.24% Traditional cash on cash: 4.58% Airbnb Rental Income: $3260 Traditional Rental Income: $1900 Airbnb ROI: 7.24% Traditional ROI: 4.58%
205 LEWFIELD CIRCLE #205 Winter Park, FL Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis cou...	2 beds \| 2 baths \| 927 sq.ft.	$235,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 3.77% Airbnb Rental Income: $3260 Traditional Rental Income: $1737 Airbnb ROI: 7.33% Traditional ROI: 3.77%
7468 CANFORD COURT #24 Winter Park, FL This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spac...	2 beds \| 2 baths \| 1,365 sq.ft.	$189,999	Airbnb cash on cash: 8.35% Traditional cash on cash: 6.64% Airbnb Rental Income: $3260 Traditional Rental Income: $2220 Airbnb ROI: 8.35% Traditional ROI: 6.64%
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.	$274,900	Airbnb cash on cash: 9.47% Traditional cash on cash: 4.41% Airbnb Rental Income: $4337 Traditional Rental Income: $2116 Airbnb ROI: 9.47% Traditional ROI: 4.41%
200 Saint Andrews Boulevard #315 Winter Park, FL One or more photos were virtually stagesExperience elevated living in this beautifully...	1 beds \| 1 baths \| 793 sq.ft.	$169,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 1.65% Airbnb Rental Income: $2412 Traditional Rental Income: $1312 Airbnb ROI: 4.81% Traditional ROI: 1.65%
4864 TANGERINE AVENUE #4864 Winter Park, FL One or more photo(s) has been virtually staged. 4.99% INTEREST RATE OFFERED FOR QUALIFIED ...	2 beds \| 2 baths \| 1,059 sq.ft.	$200,000	Airbnb cash on cash: 7.85% Traditional cash on cash: 5.11% Airbnb Rental Income: $3260 Traditional Rental Income: $2008 Airbnb ROI: 7.85% Traditional ROI: 5.11%
188 LEWFIELD CIRCLE #188 Winter Park, FL Welcome to 188 Lewfield Cir â a beautifully designed 1-bedroom, 1-bath condo located in ...	1 beds \| 1 baths \| 678 sq.ft.	$139,000	Airbnb cash on cash: 8.71% Traditional cash on cash: 7.07% Airbnb Rental Income: $2412 Traditional Rental Income: $1603 Airbnb ROI: 8.71% Traditional ROI: 7.07%
4858 TANGERINE AVENUE #4858 Winter Park, FL Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated...	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%
7300 DANIEL WEBSTER DRIVE #M7 Winter Park, FL Welcome home to this stunningly updated two-story condo that perfectly combines modern ele...	2 beds \| 3 baths \| 1,108 sq.ft.	$165,000	Airbnb cash on cash: 9.92% Traditional cash on cash: 6.02% Airbnb Rental Income: $3260 Traditional Rental Income: $1914 Airbnb ROI: 9.92% Traditional ROI: 6.02%
3027 AARON BURR AVENUE #L1 Winter Park, FL Step into this beautifully renovated two-story condo offering the perfect blend of modern ...	2 beds \| 3 baths \| 1,090 sq.ft.	$165,000	Airbnb cash on cash: 9.92% Traditional cash on cash: 5.98% Airbnb Rental Income: $3260 Traditional Rental Income: $1907 Airbnb ROI: 9.92% Traditional ROI: 5.98%
200 SAINT ANDREWS BOULEVARD #2901 Winter Park, FL Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park,...	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%
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.	$285,000	Airbnb cash on cash: 7.83% Traditional cash on cash: 4.63% Airbnb Rental Income: $3260 Traditional Rental Income: $1668 Airbnb ROI: 7.83% Traditional ROI: 4.63%
7794 COUNTRY PLACE #2 Winter Park, FL Winter Park Clean, updated condo in Move In Condition - The newest condo's year built are ...	2 beds \| 2 baths \| 1,068 sq.ft.	$241,900	Airbnb cash on cash: 7.14% Traditional cash on cash: 3.19% Airbnb Rental Income: $3260 Traditional Rental Income: $1625 Airbnb ROI: 7.14% Traditional ROI: 3.19%
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.	$279,000	Airbnb cash on cash: 7.86% Traditional cash on cash: 5.27% Airbnb Rental Income: $3260 Traditional Rental Income: $1846 Airbnb ROI: 7.86% Traditional ROI: 5.27%
151 LEWFIELD CIRCLE #4 Winter Park, FL Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1...	1 beds \| 1 baths \| 678 sq.ft.	$139,000	Airbnb cash on cash: 8.19% Traditional cash on cash: 5.36% Airbnb Rental Income: $2412 Traditional Rental Income: $1444 Airbnb ROI: 8.19% Traditional ROI: 5.36%
200 SAINT ANDREW #3103 Winter Park, FL Under contract-accepting backup offers. Welcome to this charming Seasons unit townhome o...	2 beds \| 2 baths \| 1,219 sq.ft.	$190,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 4.98% Airbnb Rental Income: $3260 Traditional Rental Income: $1909 Airbnb ROI: 8.41% Traditional ROI: 4.98%
5130 LAZY OAKS DRIVE #5130 Winter Park, FL Under contract-accepting backup offers. Low HOA!!! Spacious 2-bedroom unit offering 1,008 ...	2 beds \| 2 baths \| 1,008 sq.ft.	$230,000	Airbnb cash on cash: 8.45% Traditional cash on cash: 6.07% Airbnb Rental Income: $3260 Traditional Rental Income: $2010 Airbnb ROI: 8.45% Traditional ROI: 6.07%
5180 LAZY OAKS DRIVE #5180 Winter Park, FL Welcome to your Florida retreat. Whether youâre searching for the perfect first home or...	2 beds \| 2 baths \| 1,008 sq.ft.	$290,000	Airbnb cash on cash: 6.19% Traditional cash on cash: 4.27% Airbnb Rental Income: $3260 Traditional Rental Income: $2005 Airbnb ROI: 6.19% Traditional ROI: 4.27%

Your search for investment property begins and ends here

Airbnb Condo For Sale in Winter Park, FL

150 KILLARNEY BAY COURT #5

Winter Park, FL

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

$335,000

Airbnb cash on cash: 4.49%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $3260

Traditional Rental Income: $2233

Airbnb ROI: 4.49%

Traditional ROI: 3.55%

2500 LEE ROAD #208

Winter Park, FL

2 beds | 2 baths | 956 sq.ft.

$180,000

Airbnb cash on cash: 9.58%

Traditional cash on cash: 7.87%

Airbnb Rental Income: $3260

Traditional Rental Income: $2235

Airbnb ROI: 9.58%

Traditional ROI: 7.87%

311 E MORSE BOULEVARD #7-5

Winter Park, FL

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%

151 N ORLANDO AVENUE #115

Winter Park, FL

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%

851 MILES AVENUE #13

Winter Park, FL

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%

2500 LEE RD. #222

Winter Park, FL

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%

1809 Hammerlin Ave

Winter Park, FL

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

$585,000

Airbnb cash on cash: 3.4%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $4337

Traditional Rental Income: $2615

Airbnb ROI: 3.4%

Traditional ROI: 1.92%

630 KILLARNEY BAY COURT #3

Winter Park, FL

2 beds | 3 baths | 1,428 sq.ft.

$495,000

Airbnb cash on cash: 1.87%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $3260

Traditional Rental Income: $2514

Airbnb ROI: 1.87%