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

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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%
1742 Temple Dr Winter Park, FL Contemporary-Modern Masterpiece in the Heart of Winter Park. Custom built and remodeled in...	4 beds \| 5 baths \| 3,658 sq.ft.	$3,449,999	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.52% Airbnb Rental Income: $5745 Traditional Rental Income: $6290 Airbnb ROI: -0.01% Traditional ROI: 0.52%
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%
1761 Legion Dr Winter Park, FL One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, ...	5 beds \| 5 baths \| 4,955 sq.ft.	$3,270,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.01% Airbnb Rental Income: $null Traditional Rental Income: $11249 Airbnb ROI: N/A Traditional ROI: 2.01%
550 Palmer Ave Winter Park, FL Beautiful home just minutes away from Downtown Winter Park. As you enter this stunning hom...	5 beds \| 6 baths \| 5,939 sq.ft.	$6,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $12343 Airbnb ROI: N/A Traditional ROI: 0.73%
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%
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.	$1,399,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 2.44% Airbnb Rental Income: $5745 Traditional Rental Income: $4790 Airbnb ROI: 2.3% Traditional ROI: 2.44%
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%
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%
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%
106 S Interlachen Ave #118 Winter Park, FL Dream come true! Downtown Winter Park 3BR/2BA home (Currently staged as a large 2 bedroom ...	3 beds \| 2 baths \| 1,834 sq.ft.	$1,395,000	Airbnb cash on cash: -0.4% Traditional cash on cash: -1.35% Airbnb Rental Income: $4337 Traditional Rental Income: $2197 Airbnb ROI: -0.4% Traditional ROI: -1.35%
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%
432 Worthington Dr Winter Park, FL Under contract-accepting backup offers. Discover a charming, single story home in the hear...	5 beds \| 4 baths \| 3,845 sq.ft.	$2,719,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.51% Airbnb Rental Income: $null Traditional Rental Income: $1950 Airbnb ROI: N/A Traditional ROI: -0.51%
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%
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.	$3,174,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.25% Airbnb Rental Income: $5745 Traditional Rental Income: $5609 Airbnb ROI: -0.09% Traditional ROI: 0.25%
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%
541 W Canton Ave Winter Park, FL Timeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new...	4 beds \| 3 baths \| 3,553 sq.ft.	$2,800,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 0.58% Airbnb Rental Income: $5745 Traditional Rental Income: $4634 Airbnb ROI: 0.57% Traditional ROI: 0.58%
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%
234 Detmar Dr Winter Park, FL Beautiful 1930âs Winter Park Character Home on Oversized 0.42 acre lot with privacy gate...	4 beds \| 5 baths \| 3,609 sq.ft.	$1,599,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.07% Airbnb Rental Income: $5745 Traditional Rental Income: $10197 Airbnb ROI: 1.3% Traditional ROI: 5.07%
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%
2600 Euston Rd Winter Park, FL	6 beds \| 3 baths \| 3,145 sq.ft.	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $3880 Airbnb ROI: N/A Traditional ROI: 4.56%
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 \| 2,895 sq.ft.	$1,479,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.62% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 1.62%
250 CORTLAND AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave â a refined...	3 beds \| 2 baths \| 2,114 sq.ft.	$950,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.4% Airbnb Rental Income: $4337 Traditional Rental Income: $3501 Airbnb ROI: 2.31% Traditional ROI: 2.4%
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%
40 Palmer Ave Winter Park, FL Under contract-accepting backup offers. Walk to Park Avenue â 40 Palmer Avenue, Winter P...	5 beds \| 5 baths \| 5,905 sq.ft.	$6,950,000	Airbnb cash on cash: N/A Traditional cash on cash: 0% Airbnb Rental Income: $null Traditional Rental Income: $7586 Airbnb ROI: N/A Traditional ROI: 0%
2612 Roxbury Rd Winter Park, FL Welcome to this charming Winter park home in the desired neighborhood of 32789. Ideally si...	5 beds \| 3 baths \| 2,472 sq.ft.	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $3816 Airbnb ROI: N/A Traditional ROI: 4.54%

Real Estate investment in Winter-park, FL

There are 359 properties for sale in the city of Winter Park . The median list price in Winter Park is $639,900 and the average price per square foot is $294. In May 2026, the average monthly cash on cash return in Winter Park is 2.00%. The average monthly rental income in Winter Park is $2,412.

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

There are 359 investment properties available for sale in Winter-park.

In 2026, the best neighborhood to buy investment property is Winter Park.

The ROI for Short-Term is higher than the Long-Term in Winter-park with average rental income of $4,337.

Your search for investment property begins and ends here

Investment Property 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%

1742 Temple Dr

Winter Park, FL

4 beds | 5 baths | 3,658 sq.ft.

$3,449,999

Airbnb cash on cash: -0.01%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $5745

Traditional Rental Income: $6290

Airbnb ROI: -0.01%

Traditional ROI: 0.52%

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%

1761 Legion Dr

Winter Park, FL

5 beds | 5 baths | 4,955 sq.ft.

$3,270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.01%

Airbnb Rental Income: $null

Traditional Rental Income: $11249

Airbnb ROI: N/A

Traditional ROI: 2.01%

550 Palmer Ave

Winter Park, FL

5 beds | 6 baths | 5,939 sq.ft.

$6,495,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.73%

Airbnb Rental Income: $null

Traditional Rental Income: $12343

Airbnb ROI: N/A