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
640 ARJAY WAY Winter Park, FL Price Improvement on this amazing oversized lot! Located in one of Winter Parkâs most de...	5 beds \| 5 baths \| 3,953 sq.ft.	$1,974,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.77% Airbnb Rental Income: $null Traditional Rental Income: $8073 Airbnb ROI: N/A Traditional ROI: 2.77%
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.	$1,475,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 1.07% Airbnb Rental Income: $5745 Traditional Rental Income: $3779 Airbnb ROI: 1.66% Traditional ROI: 1.07%
3114 HEARTLEAF PLACE Winter Park, FL Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in L...	4 beds \| 3 baths \| 2,702 sq.ft.	$699,900	Airbnb cash on cash: 4.92% Traditional cash on cash: 3.05% Airbnb Rental Income: $5745 Traditional Rental Income: $3378 Airbnb ROI: 4.92% Traditional ROI: 3.05%
1018 TURNER ROAD Winter Park, FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 2,237 sq.ft.	$835,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 2.32% Airbnb Rental Income: $4337 Traditional Rental Income: $3458 Airbnb ROI: 2.27% Traditional ROI: 2.32%
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.	$1,450,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.07% Airbnb Rental Income: $5745 Traditional Rental Income: $4447 Airbnb ROI: 2.18% Traditional ROI: 2.07%
744 CORNWALL ROAD Winter Park, FL Welcome to your dream home! This exceptional 4-bedroom residence features a desirable spli...	4 beds \| 2 baths \| 1,968 sq.ft.	$715,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 2.66% Airbnb Rental Income: $5745 Traditional Rental Income: $3028 Airbnb ROI: 5.01% Traditional ROI: 2.66%
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: 7.4% Airbnb Rental Income: $2412 Traditional Rental Income: $1632 Airbnb ROI: 8.99% Traditional ROI: 7.4%
2919 BOWER ROAD Winter Park, FL Beautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of...	3 beds \| 2 baths \| 2,325 sq.ft.	$779,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 2.59% Airbnb Rental Income: $4337 Traditional Rental Income: $3617 Airbnb ROI: 2.33% Traditional ROI: 2.59%
668 OVERSPIN DRIVE Winter Park, FL One or more photo(s) has been virtually staged. A contemporary, beautifully finished home ...	4 beds \| 3 baths \| 2,509 sq.ft.	$875,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.01% Airbnb Rental Income: $5745 Traditional Rental Income: $3620 Airbnb ROI: 3.21% Traditional ROI: 2.01%
418 GILBERT ROAD Winter Park, FL Beautifully renovated solid block home on a quiet street in highly desirable Winter Park P...	3 beds \| 3 baths \| 1,680 sq.ft.	$740,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.09% Airbnb Rental Income: $4337 Traditional Rental Income: $3068 Airbnb ROI: 2.61% Traditional ROI: 2.09%
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: 3.18% Airbnb Rental Income: $3260 Traditional Rental Income: $2118 Airbnb ROI: 4.49% Traditional ROI: 3.18%
1521 CHESTNUT AVENUE Winter Park, FL Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thou...	4 beds \| 3 baths \| 2,842 sq.ft.	$1,849,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.57% Airbnb Rental Income: $5745 Traditional Rental Income: $4691 Airbnb ROI: 0.52% Traditional ROI: 0.57%
1518 PINEWOOD DRIVE Winter Park, FL Income-producing home with a detached in-law apartment in a prime central Orlando location...	3 beds \| N/A baths \| 1,197 sq.ft.	$415,000	Airbnb cash on cash: 8.94% Traditional cash on cash: 3.55% Airbnb Rental Income: $5745 Traditional Rental Income: $2501 Airbnb ROI: 8.94% Traditional ROI: 3.55%
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: 5.3% Airbnb Rental Income: $3260 Traditional Rental Income: $1912 Airbnb ROI: 8.73% Traditional ROI: 5.3%
346 S RANGER BOULEVARD Winter Park, FL PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park...	3 beds \| 2 baths \| 1,592 sq.ft.	$485,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.97% Airbnb Rental Income: $4337 Traditional Rental Income: $2845 Airbnb ROI: 5.25% Traditional ROI: 3.97%
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.	$179,900	Airbnb cash on cash: 8.72% Traditional cash on cash: 4.89% Airbnb Rental Income: $3260 Traditional Rental Income: $1873 Airbnb ROI: 8.72% Traditional ROI: 4.89%
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.	$144,000	Airbnb cash on cash: 8.2% Traditional cash on cash: 5.25% Airbnb Rental Income: $2412 Traditional Rental Income: $1414 Airbnb ROI: 8.2% Traditional ROI: 5.25%
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.	$3,199,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 0.14% Airbnb Rental Income: $5745 Traditional Rental Income: $5293 Airbnb ROI: -0.1% Traditional ROI: 0.14%
5418 ARDMORE DRIVE Winter Park, FL One or more photo(s) has been virtually staged. WELCOME HOME A generous .23 ACRE LOT, ...	3 beds \| 2 baths \| 1,560 sq.ft.	$450,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 3.6% Airbnb Rental Income: $4337 Traditional Rental Income: $2424 Airbnb ROI: 5.98% Traditional ROI: 3.6%
1354 TIERRA CIRCLE Winter Park, FL Located in the highly sought-after Casa Aloma community, this charming 1960s home offers t...	4 beds \| 2 baths \| 1,827 sq.ft.	$435,000	Airbnb cash on cash: 9.18% Traditional cash on cash: 4.53% Airbnb Rental Income: $5745 Traditional Rental Income: $2701 Airbnb ROI: 9.18% Traditional ROI: 4.53%
1849 VIBURNUM LANE Winter Park, FL This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright...	4 beds \| 2 baths \| 1,627 sq.ft.	$425,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 4.18% Airbnb Rental Income: $5745 Traditional Rental Income: $2495 Airbnb ROI: 9.46% Traditional ROI: 4.18%
720 W WEBSTER AVENUE Winter Park, FL One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME ...	3 beds \| 2 baths \| 1,356 sq.ft.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 3.2% Airbnb Rental Income: $4337 Traditional Rental Income: $2727 Airbnb ROI: 4.56% Traditional ROI: 3.2%
2217 SUSSEX ROAD Winter Park, FL PRICE REDUCED!!! 4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THI...	4 beds \| 2 baths \| 2,092 sq.ft.	$520,000	Airbnb cash on cash: 7.32% Traditional cash on cash: 4.4% Airbnb Rental Income: $5745 Traditional Rental Income: $3177 Airbnb ROI: 7.32% Traditional ROI: 4.4%
3463 ARNEL DRIVE Winter Park, FL Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus r...	3 beds \| 2 baths \| 1,770 sq.ft.	$479,900	Airbnb cash on cash: 5.45% Traditional cash on cash: 4.78% Airbnb Rental Income: $4337 Traditional Rental Income: $3121 Airbnb ROI: 5.45% Traditional ROI: 4.78%
1800 MAGNOLIA AVENUE Winter Park, FL One or more photo(s) has been virtually staged. Experience refined living in this exquisit...	4 beds \| 3 baths \| 2,431 sq.ft.	$1,150,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.83% Airbnb Rental Income: $5745 Traditional Rental Income: $4205 Airbnb ROI: 2.2% Traditional ROI: 1.83%
311 E MORSE BOULEVARD #7-2 Winter Park, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. En...	1 beds \| 1 baths \| 900 sq.ft.	$399,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.5% Airbnb Rental Income: $2412 Traditional Rental Income: $2105 Airbnb ROI: -0.26% Traditional ROI: 0.5%
675 OVERSPIN DRIVE Winter Park, FL Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatil...	4 beds \| 4 baths \| 3,062 sq.ft.	$775,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 2.99% Airbnb Rental Income: $5745 Traditional Rental Income: $4046 Airbnb ROI: 3.75% Traditional ROI: 2.99%
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: -0.07% Airbnb Rental Income: $4337 Traditional Rental Income: $3213 Airbnb ROI: 0.04% Traditional ROI: -0.07%
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: 4.38% Airbnb Rental Income: $2412 Traditional Rental Income: $1453 Airbnb ROI: 6.87% Traditional ROI: 4.38%
2126 N HAMPTON CIRCLE Winter Park, FL Under contract-accepting backup offers. Step into your own private retreat in the sought-a...	3 beds \| 2 baths \| 1,745 sq.ft.	$500,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 3.23% Airbnb Rental Income: $4337 Traditional Rental Income: $2513 Airbnb ROI: 5.18% Traditional ROI: 3.23%
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.	$1,499,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $4288 Airbnb ROI: N/A Traditional ROI: 1.63%
1636 Elizabeths Walk Winter Park, FL Welcome home to this custom 4-bedroom, 4.5-bath home in the highly desirable community of ...	4 beds \| 4 baths \| 3,412 sq.ft.	$2,195,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.46% Airbnb Rental Income: $5745 Traditional Rental Income: $4396 Airbnb ROI: 0.56% Traditional ROI: 0.46%
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: 2.14% Airbnb Rental Income: $4337 Traditional Rental Income: $3274 Airbnb ROI: 2.31% Traditional ROI: 2.14%
1150 VIA SALERNO Winter Park, FL In the heart of Winter Parkâs coveted Vias neighborhood, 1150 Via Salerno is a newly com...	4 beds \| 6 baths \| 3,850 sq.ft.	$4,750,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.21% Airbnb Rental Income: $5745 Traditional Rental Income: $10746 Airbnb ROI: -0.19% Traditional ROI: 1.21%
3019 ANTIQUE OAKS CIRCLE #124 Winter Park, FL The Ultimate Winter Park is your every desire. Investment Potential, Student Sanctuary or ...	1 beds \| 1 baths \| 749 sq.ft.	$154,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 6.43% Airbnb Rental Income: $2412 Traditional Rental Income: $1712 Airbnb ROI: 7.17% Traditional ROI: 6.43%
1174 WILDMEADOW RUN Winter Park, FL Welcome to 1174 Wildmeadow Run in Winter Parkâs gated Hawkâs Crest community. Located ...	3 beds \| 3 baths \| 1,770 sq.ft.	$669,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.86% Airbnb Rental Income: $4337 Traditional Rental Income: $2663 Airbnb ROI: 3.08% Traditional ROI: 1.86%
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.	$1,449,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3138 Airbnb ROI: 1.23% Traditional ROI: 1.02%
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: 3.04% Airbnb Rental Income: $5745 Traditional Rental Income: $2718 Airbnb ROI: 7.07% Traditional ROI: 3.04%
2412 CHANTILLY AVENUE Winter Park, FL Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaV...	5 beds \| 7 baths \| 4,506 sq.ft.	$2,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $12340 Airbnb ROI: N/A Traditional ROI: 4.32%
3601 Midiron Dr Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	N/A beds \| N/A baths \| 954 sq.ft.	$489,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.02% Airbnb Rental Income: $2207 Traditional Rental Income: $1579 Airbnb ROI: 1.17% Traditional ROI: 1.02%

Real Estate investment in Winter-park, FL

There are 172 properties for sale in the city of Winter Park . The median list price in Winter Park is $557,500 and the average price per square foot is $277. In April 2026, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,342.

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

There are 172 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

640 ARJAY WAY

Winter Park, FL

5 beds | 5 baths | 3,953 sq.ft.

$1,974,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.77%

Airbnb Rental Income: $null

Traditional Rental Income: $8073

Airbnb ROI: N/A

Traditional ROI: 2.77%

1751 GOODRICH AVENUE

Winter Park, FL

4 beds | 4 baths | 2,170 sq.ft.

$1,475,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $5745

Traditional Rental Income: $3779

Airbnb ROI: 1.66%

Traditional ROI: 1.07%

3114 HEARTLEAF PLACE

Winter Park, FL

4 beds | 3 baths | 2,702 sq.ft.

$699,900

Airbnb cash on cash: 4.92%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $5745

Traditional Rental Income: $3378

Airbnb ROI: 4.92%

Traditional ROI: 3.05%

1018 TURNER ROAD

Winter Park, FL

3 beds | 2 baths | 2,237 sq.ft.

$835,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $4337

Traditional Rental Income: $3458

Airbnb ROI: 2.27%

Traditional ROI: 2.32%

1649 Harmon Ave

Winter Park, FL

4 beds | 3 baths | 3,223 sq.ft.

$1,450,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $5745

Traditional Rental Income: $4447

Airbnb ROI: 2.18%

Traditional ROI: 2.07%

744 CORNWALL ROAD

Winter Park, FL

4 beds | 2 baths | 1,968 sq.ft.

$715,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $5745

Traditional Rental Income: $3028

Airbnb ROI: 5.01%

Traditional ROI: 2.66%

1000 S SEMORAN BOULEVARD #715

Winter Park, FL

1 beds | 1 baths | 735 sq.ft.

$122,990

Airbnb cash on cash: 8.99%

Traditional cash on cash: 7.4%

Airbnb Rental Income: $2412

Traditional Rental Income: $1632

Airbnb ROI: 8.99%

Traditional ROI: 7.4%

2919 BOWER ROAD

Winter Park, FL

3 beds | 2 baths | 2,325 sq.ft.

$779,000

Airbnb cash on cash: 2.33%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $4337

Traditional Rental Income: $3617

Airbnb ROI: 2.33%