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.

Golden Highlands Investment Property for Sale in Winter Park, FL

Search for Golden Highlands Investment Property for Sale in Winter Park, Florida. Browse all of Mashvisor’s Golden Highlands Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 196 Golden Highlands Investment Property 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
640 ARJAY WAY Winter Park, FL Motivated Sellers! Priced at $35,000 below recent Appraisal Price on this amazing oversize...	5 beds \| 5 baths \| 3,953 sq.ft.	$1,890,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.8% Airbnb Rental Income: $null Traditional Rental Income: $7827 Airbnb ROI: N/A Traditional ROI: 2.8%
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 AVENUE 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%
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%
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%
1437 MILLER AVENUE Winter Park, FL A rare infill opportunity in one of Central Florida's most desirable communities. This 0.3...	5 beds \| 4 baths \| 2,150 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $4555 Airbnb ROI: N/A Traditional ROI: 4.46%
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%
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.	$1,799,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.78% Airbnb Rental Income: $5745 Traditional Rental Income: $4967 Airbnb ROI: 0.56% Traditional ROI: 0.78%
266 W LYMAN AVENUE 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: 0.26% Traditional cash on cash: -0.07% Airbnb Rental Income: $4337 Traditional Rental Income: $2999 Airbnb ROI: 0.26% Traditional ROI: -0.07%
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%
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%
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: 1.58% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 1.58%
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: 0.57% Airbnb Rental Income: $5745 Traditional Rental Income: $4606 Airbnb ROI: 0.56% Traditional ROI: 0.57%
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%
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%
1250 Formosa Ave Winter Park, FL Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nest...	3 beds \| 3 baths \| 1,937 sq.ft.	$560,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.02% Airbnb Rental Income: $4337 Traditional Rental Income: $3249 Airbnb ROI: 3.36% Traditional ROI: 3.02%
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.	$1,349,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 1.38% Airbnb Rental Income: $4337 Traditional Rental Income: $3402 Airbnb ROI: 1.4% Traditional ROI: 1.38%
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%
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.	$2,394,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $13144 Airbnb ROI: N/A Traditional ROI: 4.68%
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: 1.52% Airbnb Rental Income: $2207 Traditional Rental Income: $1811 Airbnb ROI: 1.17% Traditional ROI: 1.52%
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%
1010 Garden Dr Winter Park, FL 1010 Garden Dr, Orlando, FL 32789 \| Other	N/A beds \| N/A baths \| N/A	$485,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 1.33% Airbnb Rental Income: $2207 Traditional Rental Income: $1553 Airbnb ROI: 1.55% Traditional ROI: 1.33%
1810 HOLLYWOOD AVENUE Winter Park, FL Under Construction. Estimated completion August!! Experience modern luxury living in the h...	4 beds \| 4 baths \| 2,604 sq.ft.	$1,689,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.73% Airbnb Rental Income: $5745 Traditional Rental Income: $5013 Airbnb ROI: 1.47% Traditional ROI: 1.73%
1885 TEMPLE DRIVE Winter Park, FL Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, thi...	5 beds \| 4 baths \| 3,691 sq.ft.	$2,265,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $6564 Airbnb ROI: N/A Traditional ROI: 1.81%
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%
1782 PINE AVENUE Winter Park, FL Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where ...	5 beds \| 7 baths \| 4,782 sq.ft.	$4,197,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $12218 Airbnb ROI: N/A Traditional ROI: 2%
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%
1399 ALOMA AVENUE Winter Park, FL *Price Adjustment * Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, ...	3 beds \| 2 baths \| 1,804 sq.ft.	$600,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 4.09% Airbnb Rental Income: $4337 Traditional Rental Income: $3142 Airbnb ROI: 4.6% Traditional ROI: 4.09%
1768 MONDRIAN CIRCLE Winter Park, FL One or more photo(s) has been virtually staged. Step into refined lakeside living at the e...	3 beds \| 4 baths \| 2,193 sq.ft.	$1,099,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1.61% Airbnb Rental Income: $4337 Traditional Rental Income: $4159 Airbnb ROI: 0.89% Traditional ROI: 1.61%
2211 Azalea Pl Winter Park, FL Luxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe...	5 beds \| 7 baths \| 7,278 sq.ft.	$5,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $13911 Airbnb ROI: N/A Traditional ROI: 1.16%
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. Step into a life where charm meets convenience in the heart...	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%
1161 VALENCIA AVENUE Winter Park, FL Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, bu...	4 beds \| 5 baths \| 4,181 sq.ft.	$4,270,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.34% Airbnb Rental Income: $5745 Traditional Rental Income: $8217 Airbnb ROI: -0.57% Traditional ROI: 0.34%
607 ELLEN DRIVE Winter Park, FL NEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new const...	4 beds \| 5 baths \| 2,812 sq.ft.	$1,499,900	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.14% Airbnb Rental Income: $5745 Traditional Rental Income: $6330 Airbnb ROI: 1.89% Traditional ROI: 3.14%
3018 NORTHWOOD BOULEVARD Winter Park, FL "MOTIVATED SELLER" - NEED SOME CLOSING COST? RATE BUY DOWN? WE CAN HELP GET YOU INTO THIS ...	3 beds \| 2 baths \| 1,761 sq.ft.	$678,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.11% Airbnb Rental Income: $4337 Traditional Rental Income: $3308 Airbnb ROI: 3.3% Traditional ROI: 3.11%
1134 WASHINGTON AVENUE #13 Winter Park, FL Discover this generously sized 3-bedroom, 3.5-bath townhome offering 2,083 square feet of ...	3 beds \| 4 baths \| 2,083 sq.ft.	$625,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 4.08% Airbnb Rental Income: $4337 Traditional Rental Income: $4518 Airbnb ROI: 2.21% Traditional ROI: 4.08%
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%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Winter Park, FL

640 ARJAY WAY

Winter Park, FL

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

$1,890,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.8%

Airbnb Rental Income: $null

Traditional Rental Income: $7827

Airbnb ROI: N/A

Traditional ROI: 2.8%

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 AVENUE

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%

1649 Harmon Ave

Winter Park, FL

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%

1441 CARDINAL COURT

Winter Park, FL

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%

1437 MILLER AVENUE

Winter Park, FL

5 beds | 4 baths | 2,150 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.46%

Airbnb Rental Income: $null

Traditional Rental Income: $4555

Airbnb ROI: N/A

Traditional ROI: 4.46%

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%

1521 CHESTNUT AVENUE

Winter Park, FL

4 beds | 3 baths | 2,842 sq.ft.

$1,799,900

Airbnb cash on cash: 0.56%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $5745

Traditional Rental Income: $4967

Airbnb ROI: 0.56%