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 For Sale in Winter Park, FL

Q: What is the average Airbnb occupancy rate in Winter-park, FL?

In May 2026, the average Airbnb occupancy rate in Winter-park is 86%.

Q: How to get Winter-park, FL Airbnb data?

Airbnb data on vacation rentals in Winter-park, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-park, FL market insights, guest information and booking details, seasonality trends and historical Winter-park, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1900 Winter Park Rd Winter Park, FL 1900 Winter Park Rd, Winter Park, FL 32789 \| Single Family Residential	4 beds \| 2 baths \| 1,511 sq.ft.	$941,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 0.8% Airbnb Rental Income: $5745 Traditional Rental Income: $2448 Airbnb ROI: 3.26% Traditional ROI: 0.8%
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%
1307 Formosa Ave Winter Park, FL Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximat...	2 beds \| 1 baths \| 1,150 sq.ft.	$375,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 3.4% Airbnb Rental Income: $3260 Traditional Rental Income: $2199 Airbnb ROI: 4.33% Traditional ROI: 3.4%
1840 Bryan Ave Winter Park, FL 1840 Bryan Ave, Winter Park, FL 32789 \| Single Family Residential	4 beds \| 3 baths \| 3,727 sq.ft.	$1,849,000	Airbnb cash on cash: 0.74% Traditional cash on cash: -0.2% Airbnb Rental Income: $5745 Traditional Rental Income: $2986 Airbnb ROI: 0.74% Traditional ROI: -0.2%
432 W Swoope Ave Winter Park, FL A short stroll to Park Avenue in 5 minutes!!!!! This beautiful modern Townhouse is fee sim...	4 beds \| 3 baths \| 2,317 sq.ft.	$695,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.21% Airbnb Rental Income: $5745 Traditional Rental Income: $3988 Airbnb ROI: 4.15% Traditional ROI: 3.21%
1611 Chestnut Ave Winter Park, FL GREAT 3/2 HOME LOCATED IN LAKE KNOWLES TERRACE SUBDIVISION ON A TREE-LINED BRICK STREET IN...	4 beds \| 4 baths \| 2,916 sq.ft.	$1,100,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.03% Airbnb Rental Income: $5745 Traditional Rental Income: $3341 Airbnb ROI: 3.26% Traditional ROI: 2.03%
1725 Carollee Ln Winter Park, FL Open and spacious Green Terrace home is a perfect blend of character, sophistication and m...	3 beds \| 2 baths \| 2,335 sq.ft.	$1,015,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 0.99% Airbnb Rental Income: $4337 Traditional Rental Income: $2589 Airbnb ROI: 1.88% Traditional ROI: 0.99%
1836 Grinnell Ter Winter Park, FL A fully updated jewel box bungalow located in the heart of Winter Park on a beautiful tree...	3 beds \| 2 baths \| 1,907 sq.ft.	$999,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 0.71% Airbnb Rental Income: $4337 Traditional Rental Income: $2284 Airbnb ROI: 1.94% Traditional ROI: 0.71%
2408 Lafayette Ave Winter Park, FL The Drive up is great with the gables and stone work. The oversized family room is open to...	4 beds \| 3 baths \| 2,838 sq.ft.	$1,495,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 0.93% Airbnb Rental Income: $5745 Traditional Rental Income: $2819 Airbnb ROI: 2.21% Traditional ROI: 0.93%
2111 Mallard Cir Winter Park, FL One-of-a-Kind Winter Park home nestled between the tree-lined streets of desirable Quail H...	4 beds \| 3 baths \| 2,667 sq.ft.	$1,295,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 1.22% Airbnb Rental Income: $5745 Traditional Rental Income: $3088 Airbnb ROI: 2.48% Traditional ROI: 1.22%
446 Melrose Ave Winter Park, FL Feel the timeless elegance of this contemporary style home nestled on a quiet street in th...	4 beds \| 2 baths \| 2,640 sq.ft.	$1,695,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 0.35% Airbnb Rental Income: $5745 Traditional Rental Income: $2598 Airbnb ROI: 1.62% Traditional ROI: 0.35%
1840 Anzle Ave Winter Park, FL Investor's opportunity in desirable Sylvan Heights! Zoned R-1A, this 6,592 sq.ft. lot is w...	4 beds \| 2 baths \| 2,350 sq.ft.	$1,750,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 0.75% Airbnb Rental Income: $5745 Traditional Rental Income: $3090 Airbnb ROI: 1.68% Traditional ROI: 0.75%
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.	$325,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.69% Airbnb Rental Income: $3260 Traditional Rental Income: $2233 Airbnb ROI: 4.65% Traditional ROI: 3.69%
266 W Lyman Ave Winter Park, FL ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart ...	3 beds \| 3 baths \| 2,000 sq.ft.	$1,375,000	Airbnb cash on cash: 0.29% Traditional cash on cash: -0.04% Airbnb Rental Income: $4337 Traditional Rental Income: $2999 Airbnb ROI: 0.29% Traditional ROI: -0.04%
1518 Pinewood Dr Winter Park, FL Income-producing home with a detached in-law apartment in a prime central Orlando location...	3 beds \| 2 baths \| 1,197 sq.ft.	$415,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 3.24% Airbnb Rental Income: $4337 Traditional Rental Income: $2379 Airbnb ROI: 5.93% Traditional ROI: 3.24%
408 Holt Ave Winter Park, FL EXCELLENT OPPORTUNITY TO OWN A TRIPLEX A STONE'S THROW FROM ROLLINS COLLEGE!!! PLEASE DO N...	2 beds \| N/A baths \| 1,440 sq.ft.	$745,000	Airbnb cash on cash: 2% Traditional cash on cash: 1.04% Airbnb Rental Income: $3260 Traditional Rental Income: $1865 Airbnb ROI: 2% Traditional ROI: 1.04%
2500 Lee Rd #232 Winter Park, FL Enjoy carefree living in this lovely community located on beautiful Lake Killarney. A com...	1 beds \| 1 baths \| 645 sq.ft.	$164,900	Airbnb cash on cash: 7.2% Traditional cash on cash: 5.18% Airbnb Rental Income: $2412 Traditional Rental Income: $1504 Airbnb ROI: 7.2% Traditional ROI: 5.18%
1398 Grove Ter Winter Park, FL Welcome to your slice of Paradise! This Custom Built Estate home on a quaint Brick line st...	4 beds \| 3 baths \| 3,450 sq.ft.	$2,195,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 0.1% Airbnb Rental Income: $5745 Traditional Rental Income: $3761 Airbnb ROI: 0.51% Traditional ROI: 0.1%
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%
311 E Morse Blvd #7-19 Winter Park, FL 55+.Studio at a great price! This condominium is in Winter Parkâs established Whispering...	1 beds \| 1 baths \| 482 sq.ft.	$289,900	Airbnb cash on cash: 1.08% Traditional cash on cash: -0.31% Airbnb Rental Income: $2412 Traditional Rental Income: $1443 Airbnb ROI: 1.08% Traditional ROI: -0.31%
1113 Via Del Mar Winter Park, FL LOOK! A tear down in the prestigious Vias of Winter Park. This large, 0.41 acre lakefron...	3 beds \| 2 baths \| 2,012 sq.ft.	$1,595,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 0.7% Airbnb Rental Income: $4337 Traditional Rental Income: $2874 Airbnb ROI: 1.07% Traditional ROI: 0.7%
240 Orange Terrace Dr Winter Park, FL CALLING ALL INVESTORS!!! The New Year is upon us and I've got your first 2021 Investment E...	4 beds \| 2 baths \| 1,718 sq.ft.	$484,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 5.08% Airbnb Rental Income: $5745 Traditional Rental Income: $2977 Airbnb ROI: 8.66% Traditional ROI: 5.08%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living in th...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,100,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.17% Airbnb Rental Income: $5745 Traditional Rental Income: $4421 Airbnb ROI: 2.34% Traditional ROI: 2.17%
2036 VIA TUSCANY Winter Park, FL WINTER PARK VIAâS!!! Incredible Oversized Lot is located in the âHeartâ of Winter Pa...	3 beds \| 2 baths \| 2,148 sq.ft.	$2,000,000	Airbnb cash on cash: 0.04% Traditional cash on cash: -0.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3307 Airbnb ROI: 0.04% Traditional ROI: -0.02%
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%
1651 Westchester Ave Winter Park, FL Under contract-accepting backup offers. Welcome to this exquisite Orwin Manor Cape Cod cla...	3 beds \| 2 baths \| 2,426 sq.ft.	$1,275,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.52% Airbnb Rental Income: $4337 Traditional Rental Income: $3402 Airbnb ROI: 1.54% Traditional ROI: 1.52%
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%
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%
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%
1660 Walnut Ave Winter Park, FL Under Construction. Elegant and modern new construction home perfectly situated in beautif...	4 beds \| 3 baths \| 2,249 sq.ft.	$1,650,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 0.78% Airbnb Rental Income: $5745 Traditional Rental Income: $3477 Airbnb ROI: 1.51% Traditional ROI: 0.78%
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%
1077 Minnesota Ave Winter Park, FL Under contract-accepting backup offers. Under Construction. New Construction in the Heart ...	4 beds \| 4 baths \| 3,046 sq.ft.	$1,495,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 0.74% Airbnb Rental Income: $5745 Traditional Rental Income: $3739 Airbnb ROI: 1.36% Traditional ROI: 0.74%
184 Sandlewood Trl #2 Winter Park, FL FHA, VA, and DPA approved. Nestled just minutes from the charming boutiques and award-winn...	2 beds \| 2 baths \| 1,133 sq.ft.	$314,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 3.7% Airbnb Rental Income: $3260 Traditional Rental Income: $2099 Airbnb ROI: 5.16% Traditional ROI: 3.7%
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%
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%
1261 Indiana Ave Winter Park, FL Welcome to The Townhomes at Harper Place, where elegance meets convenience in beautiful Wi...	3 beds \| 2 baths \| 1,660 sq.ft.	$539,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 1.86% Airbnb Rental Income: $4337 Traditional Rental Income: $2192 Airbnb ROI: 4.31% Traditional ROI: 1.86%
3018 Northwood Blvd Winter Park, FL "PRICE REDUCTION" ON THIS MOVE-IN READY, 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO ...	3 beds \| 2 baths \| 1,761 sq.ft.	$659,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 3.23% Airbnb Rental Income: $4337 Traditional Rental Income: $3308 Airbnb ROI: 3.42% Traditional ROI: 3.23%
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%
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%

Vacation Rentals in Winter Park

There are 246 vacation rental properties available for sale in the city of Winter Park . The median list price of Airbnb properties available for sale in Winter Park is $639,900 and the average price per square foot is $294. The cash on cash return on vacation rentals in Winter Park is 4.00%. The average monthly short term rental income in Winter Park is $4,337.

Winter Park, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 246 Airbnb properties available for sale in Winter Park.

In 2026, the best neighborhood to buy short term rental property is Winter Park.

In May 2026, the average Airbnb occupancy rate in Winter Park is 86%.

Airbnb data on vacation rentals in Winter Park, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Park, FL market insights, guest information and booking details, seasonality trends and historical Winter Park, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Park, FL

1900 Winter Park Rd

Winter Park, FL

4 beds | 2 baths | 1,511 sq.ft.

$941,000

Airbnb cash on cash: 3.26%

Traditional cash on cash: 0.8%

Airbnb Rental Income: $5745

Traditional Rental Income: $2448

Airbnb ROI: 3.26%

Traditional ROI: 0.8%

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%

1307 Formosa Ave

Winter Park, FL

2 beds | 1 baths | 1,150 sq.ft.

$375,000

Airbnb cash on cash: 4.33%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $3260

Traditional Rental Income: $2199

Airbnb ROI: 4.33%

Traditional ROI: 3.4%

1840 Bryan Ave

Winter Park, FL

4 beds | 3 baths | 3,727 sq.ft.

$1,849,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: -0.2%

Airbnb Rental Income: $5745

Traditional Rental Income: $2986

Airbnb ROI: 0.74%

Traditional ROI: -0.2%

432 W Swoope Ave

Winter Park, FL

4 beds | 3 baths | 2,317 sq.ft.

$695,000

Airbnb cash on cash: 4.15%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $5745

Traditional Rental Income: $3988

Airbnb ROI: 4.15%

Traditional ROI: 3.21%

1611 Chestnut Ave

Winter Park, FL

4 beds | 4 baths | 2,916 sq.ft.

$1,100,000

Airbnb cash on cash: 3.26%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $5745

Traditional Rental Income: $3341

Airbnb ROI: 3.26%

Traditional ROI: 2.03%

1725 Carollee Ln

Winter Park, FL

3 beds | 2 baths | 2,335 sq.ft.

$1,015,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: 0.99%

Airbnb Rental Income: $4337

Traditional Rental Income: $2589

Airbnb ROI: 1.88%

Traditional ROI: 0.99%

1836 Grinnell Ter

Winter Park, FL

3 beds | 2 baths | 1,907 sq.ft.

$999,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $4337

Traditional Rental Income: $2284

Airbnb ROI: 1.94%