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
125 S Interlachen Ave #2 Winter Park, FL Virtually Staged. Welcome to South Interlachen Place, an exceptional luxury townhome ideal...	3 beds \| 3 baths \| 3,244 sq.ft.	$3,150,000	Airbnb cash on cash: -2.11% Traditional cash on cash: -1.4% Airbnb Rental Income: $2174 Traditional Rental Income: $3704 Airbnb ROI: -2.11% Traditional ROI: -1.4%
1751 Goodrich Ave Winter Park, FL Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park...	4 beds \| 3 baths \| 2,170 sq.ft.	$1,380,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 1.18% Airbnb Rental Income: $6159 Traditional Rental Income: $3743 Airbnb ROI: 2.12% Traditional ROI: 1.18%
437 N Capen Ave Winter Park, FL Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Wi...	3 beds \| 2 baths \| 1,904 sq.ft.	$849,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.2% Airbnb Rental Income: $2174 Traditional Rental Income: $2595 Airbnb ROI: -1.02% Traditional ROI: 0.2%
1840 Bryan Ave Winter Park, FL Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests ...	4 beds \| 3 baths \| 3,727 sq.ft.	$1,725,000	Airbnb cash on cash: 0.9% Traditional cash on cash: -0.32% Airbnb Rental Income: $6159 Traditional Rental Income: $2986 Airbnb ROI: 0.9% Traditional ROI: -0.32%
1941 Oglesby Ave Winter Park, FL Welcome home to this charming 2-bedroom, 1-bathroom gem nestled in the heart of Winter Par...	2 beds \| 1 baths \| 780 sq.ft.	$340,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.11% Airbnb Rental Income: $2157 Traditional Rental Income: $1531 Airbnb ROI: 3.35% Traditional ROI: 3.11%
1441 Cardinal Ct Winter Park, FL Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet...	4 beds \| 5 baths \| 4,066 sq.ft.	$3,995,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.14% Airbnb Rental Income: $6159 Traditional Rental Income: $8729 Airbnb ROI: -0.88% Traditional ROI: 0.14%
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: 4.28% Traditional cash on cash: 3.59% Airbnb Rental Income: $2157 Traditional Rental Income: $1477 Airbnb ROI: 4.28% Traditional ROI: 3.59%
900 Carver St Winter Park, FL Completely Remodeled 2026 \| Single-Story \| Prime Location \| Dual Suites \| The redesigned k...	3 beds \| 3 baths \| 1,794 sq.ft.	$689,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.31% Airbnb Rental Income: $2174 Traditional Rental Income: $2945 Airbnb ROI: 1.25% Traditional ROI: 3.31%
2418 Euston Rd Winter Park, FL Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the...	3 beds \| 2 baths \| 2,228 sq.ft.	$624,444	Airbnb cash on cash: 0.3% Traditional cash on cash: 3.21% Airbnb Rental Income: $2174 Traditional Rental Income: $3412 Airbnb ROI: 0.3% Traditional ROI: 3.21%
2430 Chantilly Ave Winter Park, FL Architecture, design, and function come together with remarkable intention in this custom ...	4 beds \| 4 baths \| 2,916 sq.ft.	$1,598,000	Airbnb cash on cash: 1.96% Traditional cash on cash: -0.18% Airbnb Rental Income: $6159 Traditional Rental Income: $1768 Airbnb ROI: 1.96% Traditional ROI: -0.18%
2228 Azalea Pl Winter Park, FL This elegant transitional French Provincial residence was the feature home in the Orlando ...	5 beds \| 5 baths \| 5,152 sq.ft.	$5,600,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.12% Airbnb Rental Income: $null Traditional Rental Income: $7147 Airbnb ROI: N/A Traditional ROI: -0.12%
151 N Orlando Ave #118 Winter Park, FL Investment opportunity! Discover this hidden gem-a 2-bed, 1-bath condo nestled in the hear...	2 beds \| 1 baths \| 710 sq.ft.	$299,999	Airbnb cash on cash: 1.92% Traditional cash on cash: 7.24% Airbnb Rental Income: $2157 Traditional Rental Income: $3110 Airbnb ROI: 1.92% Traditional ROI: 7.24%
151 North Orlando Ave #142 Winter Park, FL Lakeside Living Meets Urban Convenience in the Heart of Winter Park! Welcome home to t...	1 beds \| 1 baths \| 582 sq.ft.	$199,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 2.45% Airbnb Rental Income: $1793 Traditional Rental Income: $1378 Airbnb ROI: 2.07% Traditional ROI: 2.45%
1885 Temple Dr Winter Park, FL Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, thi...	5 beds \| 3 baths \| 3,691 sq.ft.	$2,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $6564 Airbnb ROI: N/A Traditional ROI: 1.9%
708 BALMORAL Road Winter Park, FL A rare elevated corner lot in the heart of Winter Park - walkable to Park Avenue's boutiqu...	4 beds \| 3 baths \| 2,786 sq.ft.	$1,590,000	Airbnb cash on cash: 1.88% Traditional cash on cash: -0.02% Airbnb Rental Income: $6159 Traditional Rental Income: $2127 Airbnb ROI: 1.88% Traditional ROI: -0.02%
450 Lakewood Dr Winter Park, FL Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Flor...	5 beds \| 4 baths \| 4,572 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $9247 Airbnb ROI: N/A Traditional ROI: 2.5%
3006 Northwood Blvd Winter Park, FL Reinvented from the ground up for modern living while honoring its 1953 mid-century modern...	4 beds \| 3 baths \| 2,075 sq.ft.	$950,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 1.33% Airbnb Rental Income: $6159 Traditional Rental Income: $2644 Airbnb ROI: 3.8% Traditional ROI: 1.33%
1695 Lee Rd #D211 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.	$107,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 5% Airbnb Rental Income: $2157 Traditional Rental Income: $1449 Airbnb ROI: 6.52% Traditional ROI: 5%
1550 Palm Ave Winter Park, FL Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STRE...	4 beds \| 3 baths \| 2,706 sq.ft.	$1,829,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 0.3% Airbnb Rental Income: $6159 Traditional Rental Income: $3021 Airbnb ROI: 1.43% Traditional ROI: 0.3%
101 S New York Ave #311 Winter Park, FL Discover luxury living in this exquisitely renovated two-story condominium, ideally situat...	3 beds \| 3 baths \| 3,112 sq.ft.	$1,775,000	Airbnb cash on cash: -2.17% Traditional cash on cash: -0.78% Airbnb Rental Income: $2174 Traditional Rental Income: $4008 Airbnb ROI: -2.17% Traditional ROI: -0.78%
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 \| 2 baths \| 2,662 sq.ft.	$918,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 3.53% Airbnb Rental Income: $6159 Traditional Rental Income: $4170 Airbnb ROI: 4.44% Traditional ROI: 3.53%
2308 Mulbry Dr Winter Park, FL Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balanc...	4 beds \| 3 baths \| 2,530 sq.ft.	$1,699,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 0.24% Airbnb Rental Income: $6159 Traditional Rental Income: $2401 Airbnb ROI: 1.86% Traditional ROI: 0.24%
2007 Cornell Ave Winter Park, FL Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully...	3 beds \| 2 baths \| 1,154 sq.ft.	$449,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 0.93% Airbnb Rental Income: $2174 Traditional Rental Income: $1494 Airbnb ROI: 1.24% Traditional ROI: 0.93%
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.	$285,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.35% Airbnb Rental Income: $2157 Traditional Rental Income: $2075 Airbnb ROI: 1.61% Traditional ROI: 3.35%
560 Ololu Dr Winter Park, FL Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and abs...	2 beds \| 2 baths \| 1,086 sq.ft.	$899,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.08% Airbnb Rental Income: $2157 Traditional Rental Income: $2632 Airbnb ROI: -0.14% Traditional ROI: 1.08%
2500 Lee Rd #222 Winter Park, FL Lakefront Lifestyle in Winter Park-Under $200K! Live the resort life for less! This stunni...	1 beds \| 1 baths \| 645 sq.ft.	$184,400	Airbnb cash on cash: 3.84% Traditional cash on cash: 6.58% Airbnb Rental Income: $1793 Traditional Rental Income: $1787 Airbnb ROI: 3.84% Traditional ROI: 6.58%
1523 Miller Ave Winter Park, FL BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! Thi...	5 beds \| 4 baths \| 3,164 sq.ft.	$1,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $5740 Airbnb ROI: N/A Traditional ROI: 3.09%
726/720 N Pennsylvania Ave Winter Park, FL Opportunities like this don't come around often, this is currently the only duplex availab...	6 beds \| N/A baths \| 2,282 sq.ft.	$1,185,999	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.5% Airbnb Rental Income: $2157 Traditional Rental Income: $5535 Airbnb ROI: -0.06% Traditional ROI: 3.5%
1927 Eland Ave Winter Park, FL Ask about a lender provided credit up to $12,500 on this home!1927 Eland Avenue is a rar...	5 beds \| 3 baths \| 2,242 sq.ft.	$820,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $4225 Airbnb ROI: N/A Traditional ROI: 4.02%
1354 Indiana Ave Winter Park, FL Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to botto...	3 beds \| 2 baths \| 1,269 sq.ft.	$574,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.03% Airbnb Rental Income: $2174 Traditional Rental Income: $2752 Airbnb ROI: 0.92% Traditional ROI: 3.03%
240 N Phelps Ave Winter Park, FL A striking expression of modern luxury, this brand-new residence offers nearly 3,000 squar...	5 beds \| 4 baths \| 2,889 sq.ft.	$2,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.26% Airbnb Rental Income: $null Traditional Rental Income: $3101 Airbnb ROI: N/A Traditional ROI: 0.26%
1903 N Park Ave Winter Park, FL Completed in 2020, this beautifully designed contemporary residence on North Park Avenue o...	4 beds \| 4 baths \| 2,807 sq.ft.	$1,649,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.24% Airbnb Rental Income: $6159 Traditional Rental Income: $5163 Airbnb ROI: 1.1% Traditional ROI: 1.24%
1870 Staunton Ave Winter Park, FL Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residen...	4 beds \| 3 baths \| 2,525 sq.ft.	$1,250,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 3.56% Airbnb Rental Income: $6159 Traditional Rental Income: $5508 Airbnb ROI: 3.07% Traditional ROI: 3.56%
950 Hanover Ave Winter Park, FL Welcome home to your peaceful retreat tucked away near the end of a quiet street with view...	3 beds \| 2 baths \| 1,606 sq.ft.	$439,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 3.71% Airbnb Rental Income: $2174 Traditional Rental Income: $2358 Airbnb ROI: 1.92% Traditional ROI: 3.71%
723 Symonds Ave Winter Park, FL Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments fr...	4 beds \| 4 baths \| 3,065 sq.ft.	$1,700,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 0.38% Airbnb Rental Income: $6159 Traditional Rental Income: $3746 Airbnb ROI: 1.14% Traditional ROI: 0.38%
1571 Woodland Ave Winter Park, FL Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Wint...	5 beds \| 6 baths \| 7,397 sq.ft.	$6,000,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.09% Airbnb Rental Income: $null Traditional Rental Income: $9026 Airbnb ROI: N/A Traditional ROI: 0.09%
338 Blue Heron Dr Winter Park, FL Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Cen...	3 beds \| 3 baths \| 2,017 sq.ft.	$840,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 2.98% Airbnb Rental Income: $2174 Traditional Rental Income: $3822 Airbnb ROI: 0.17% Traditional ROI: 2.98%
1421 Chapman Cir Winter Park, FL Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the h...	4 beds \| 3 baths \| 3,578 sq.ft.	$1,377,500	Airbnb cash on cash: 1.65% Traditional cash on cash: 1.35% Airbnb Rental Income: $6159 Traditional Rental Income: $4534 Airbnb ROI: 1.65% Traditional ROI: 1.35%
1411 MILLER Avenue Winter Park, FL Built in 2023 by SGC Homes, this exceptionally livable modern Mediterranean townhome blend...	3 beds \| 4 baths \| 1,824 sq.ft.	$899,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.3% Airbnb Rental Income: $2174 Traditional Rental Income: $2977 Airbnb ROI: -0.32% Traditional ROI: 1.3%
660 W Morse Blvd Winter Park, FL Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional l...	3 beds \| 3 baths \| 3,286 sq.ft.	$2,800,000	Airbnb cash on cash: -1.55% Traditional cash on cash: -0.8% Airbnb Rental Income: $2174 Traditional Rental Income: $3561 Airbnb ROI: -1.55% Traditional ROI: -0.8%

Real Estate investment in Winter-park, FL

There are 301 properties for sale in the city of Winter Park . The median list price in Winter Park is $799,522 and the average price per square foot is $410. In September 2026, the average monthly cash on cash return in Winter Park is 3.00%. The average monthly rental income in Winter Park is $2,259.

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

There are 301 investment properties available for sale in Winter-park.

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

The ROI for Long-Term is higher than the Short-Term in Winter-park with average rental income of $2,259.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Park, FL

125 S Interlachen Ave #2

Winter Park, FL

3 beds | 3 baths | 3,244 sq.ft.

$3,150,000

Airbnb cash on cash: -2.11%

Traditional cash on cash: -1.4%

Airbnb Rental Income: $2174

Traditional Rental Income: $3704

Airbnb ROI: -2.11%

Traditional ROI: -1.4%

1751 Goodrich Ave

Winter Park, FL

4 beds | 3 baths | 2,170 sq.ft.

$1,380,000

Airbnb cash on cash: 2.12%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $6159

Traditional Rental Income: $3743

Airbnb ROI: 2.12%

Traditional ROI: 1.18%

437 N Capen Ave

Winter Park, FL

3 beds | 2 baths | 1,904 sq.ft.

$849,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $2174

Traditional Rental Income: $2595

Airbnb ROI: -1.02%

Traditional ROI: 0.2%

1840 Bryan Ave

Winter Park, FL

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

$1,725,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: -0.32%

Airbnb Rental Income: $6159

Traditional Rental Income: $2986

Airbnb ROI: 0.9%

Traditional ROI: -0.32%

1941 Oglesby Ave

Winter Park, FL

2 beds | 1 baths | 780 sq.ft.

$340,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $2157

Traditional Rental Income: $1531

Airbnb ROI: 3.35%

Traditional ROI: 3.11%

1441 Cardinal Ct

Winter Park, FL

4 beds | 5 baths | 4,066 sq.ft.

$3,995,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $6159

Traditional Rental Income: $8729

Airbnb ROI: -0.88%

Traditional ROI: 0.14%

2500 Lee Rd #220

Winter Park, FL

2 beds | 1 baths | 851 sq.ft.

$199,900

Airbnb cash on cash: 4.28%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $2157

Traditional Rental Income: $1477

Airbnb ROI: 4.28%

Traditional ROI: 3.59%

900 Carver St

Winter Park, FL

3 beds | 3 baths | 1,794 sq.ft.

$689,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $2174

Traditional Rental Income: $2945

Airbnb ROI: 1.25%