Real Estate Investment Properties for Sale in Winter Garden, FL

Looking for investment property in Winter Garden, FL with high ROI ?

Explore a variety of short-term homes & houses in Winter Garden, FL. Invest wisely with VRBO & Winter Garden, 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 Garden, FL

Search for Golden Highlands Investment Property for Sale in Winter Garden, 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 509 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
849 SHADOWMOSS DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Prime Winter Garden Location - Spacious 5-...	5 beds \| 3 baths \| 2,620 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $3077 Airbnb ROI: N/A Traditional ROI: 2.48%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on your Gorgeous 2-Story Winter Garden DREAM HOME located in the Highla...	3 beds \| 3 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.22% Airbnb Rental Income: $1636 Traditional Rental Income: $3295 Airbnb ROI: -0.5% Traditional ROI: 3.22%
15140 SUNRISE GROVE COURT Winter Garden, FL Under contract-accepting backup offers. Imagine a life where lakeside serenity meets moder...	3 beds \| 3 baths \| 2,012 sq.ft.	$390,987	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.07% Airbnb Rental Income: $1636 Traditional Rental Income: $3302 Airbnb ROI: -0.74% Traditional ROI: 5.07%
14372 SUNBRIDGE CIRCLE Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 5 baths \| 3,468 sq.ft.	$745,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 6.44% Airbnb Rental Income: $5064 Traditional Rental Income: $5980 Airbnb ROI: 3.64% Traditional ROI: 6.44%
264 BLUE STONE CIRCLE Winter Garden, FL LOCATION, LOCATION, LOCATION! Welcome to 264 Blue Stone Cir in the highly desirable Winter...	4 beds \| 3 baths \| 2,538 sq.ft.	$725,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3698 Airbnb ROI: 4.02% Traditional ROI: 3.53%
2202 ROMANUM DRIVE Winter Garden, FL Welcome to your next home in the heart of Winter Gardenâwhere location, lifestyle, and u...	3 beds \| 2 baths \| 1,889 sq.ft.	$585,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.21% Airbnb Rental Income: $1636 Traditional Rental Income: $2435 Airbnb ROI: -0.1% Traditional ROI: 2.21%
16232 ROCK COAST DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to your dream home and backyard oasis! Thi...	4 beds \| 5 baths \| 3,491 sq.ft.	$925,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.22% Airbnb Rental Income: $5064 Traditional Rental Income: $7312 Airbnb ROI: 2.41% Traditional ROI: 6.22%
373 ERON WAY #47 Winter Garden, FL Short Sale. MOVE-IN READY and quietly positioned within a well-established Winter Garden c...	2 beds \| 2 baths \| 840 sq.ft.	$163,999	Airbnb cash on cash: 5.44% Traditional cash on cash: 6.23% Airbnb Rental Income: $2340 Traditional Rental Income: $1885 Airbnb ROI: 5.44% Traditional ROI: 6.23%
2154 OAKINGTON STREET Winter Garden, FL Welcome to this beautifully maintained, single-story home that perfectly blends comfort, s...	3 beds \| 2 baths \| 1,585 sq.ft.	$469,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.23% Airbnb Rental Income: $1636 Traditional Rental Income: $2263 Airbnb ROI: -0.25% Traditional ROI: 2.23%
14501 GROVE RESORT AVENUE #1111 Winter Garden, FL Ground Floor Unit \| Pond and Fountain Views \| Aggressively Priced Ground floor residence f...	2 beds \| 2 baths \| 1,265 sq.ft.	$205,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.98% Airbnb Rental Income: $2340 Traditional Rental Income: $2636 Airbnb ROI: -0.51% Traditional ROI: 3.98%
14282 CREEKBED CIRCLE Winter Garden, FL *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing co...	4 beds \| 4 baths \| 3,479 sq.ft.	$924,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.61% Airbnb Rental Income: $5064 Traditional Rental Income: $5782 Airbnb ROI: 2.57% Traditional ROI: 4.61%
5401 BOWMAN DRIVE Winter Garden, FL Welcome to Horizon West living at its finest in the highly sought-after Overlook at Hamlin...	4 beds \| 4 baths \| 4,044 sq.ft.	$1,250,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $4606 Airbnb ROI: 1.46% Traditional ROI: 1.96%
604 FOSTER AVENUE Winter Garden, FL Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart Dis...	3 beds \| 2 baths \| 1,275 sq.ft.	$400,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.92% Airbnb Rental Income: $1636 Traditional Rental Income: $2092 Airbnb ROI: 1.48% Traditional ROI: 3.92%
13536 SUNSET LAKES CIRCLE Winter Garden, FL Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes com...	5 beds \| 4 baths \| 3,389 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $6227 Airbnb ROI: N/A Traditional ROI: 3.52%
13377 Lake Butler Blvd Winter Garden, FL One or more photo(s) has been virtually staged. BACK ON MARKET: Buyer's inability to obtai...	5 beds \| 4 baths \| 6,000 sq.ft.	$5,995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $7090 Airbnb ROI: N/A Traditional ROI: 0.02%
7266 DESERT MANDARIN STREET Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
14447 PRUNNINGWOOD PLACE Winter Garden, FL One or more photo(s) has been virtually staged. This stylish townhome in the highly sought...	2 beds \| 3 baths \| 1,250 sq.ft.	$340,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.01% Airbnb Rental Income: $2340 Traditional Rental Income: $2464 Airbnb ROI: 1.81% Traditional ROI: 4.01%
15508 PEBBLE RIDGE STREET Winter Garden, FL This is the one youâve been waiting for. A beautifully maintained four bedroom pool home...	4 beds \| 3 baths \| 2,763 sq.ft.	$695,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.14% Airbnb Rental Income: $5064 Traditional Rental Income: $3612 Airbnb ROI: 3.79% Traditional ROI: 3.14%
900 WALKERS GROVE LANE Winter Garden, FL Downtown Winter Garden â Golf Cart District! Donât miss this amazing opportunity to...	3 beds \| 3 baths \| 1,905 sq.ft.	$485,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 4.1% Airbnb Rental Income: $1636 Traditional Rental Income: $3086 Airbnb ROI: -0.11% Traditional ROI: 4.1%
8170 BLUEJACK OAK DRIVE Winter Garden, FL Welcome to 8170 Bluejack Oak Drive, a beautifully situated corner unit in the heart of the...	3 beds \| 3 baths \| 1,853 sq.ft.	$465,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2487 Airbnb ROI: -0.33% Traditional ROI: 2.68%
16554 RAVEN ROCK PLACE Winter Garden, FL Twinwaters Former MODEL home built with BEAUTIFUL UPGRADES 3 car garage ** Heated PO...	4 beds \| 3 baths \| 3,032 sq.ft.	$875,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 3.35% Airbnb Rental Income: $5064 Traditional Rental Income: $4466 Airbnb ROI: 2.82% Traditional ROI: 3.35%
14501 GROVE RESORT AVENUE #3202 Winter Garden, FL Welcome to Your Perfect Orlando Investment & Vacation Escape! This beautifully appointed c...	3 beds \| 2 baths \| 1,396 sq.ft.	$350,000	Airbnb cash on cash: -2.56% Traditional cash on cash: 2.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2677 Airbnb ROI: -2.56% Traditional ROI: 2.02%
213 W TILDEN STREET Winter Garden, FL Located in DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combi...	4 beds \| 2 baths \| 2,151 sq.ft.	$765,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $3152 Airbnb ROI: 3.47% Traditional ROI: 2.24%
15852 SHOREBIRD LANE Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 5 baths \| 2,766 sq.ft.	$779,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.76% Airbnb Rental Income: $5064 Traditional Rental Income: $4262 Airbnb ROI: 2.44% Traditional ROI: 2.76%
15372 GILLIGAN COURT Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 4 baths \| 2,781 sq.ft.	$870,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 4.09% Airbnb Rental Income: $5064 Traditional Rental Income: $5070 Airbnb ROI: 2.81% Traditional ROI: 4.09%
5531 CYPRESS HILL ROAD Winter Garden, FL Under contract-accepting backup offers. Exquisitely upgraded 4-bedroom, 3-bath smart home ...	4 beds \| 3 baths \| 2,204 sq.ft.	$610,000	Airbnb cash on cash: 4.14% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $3393 Airbnb ROI: 4.14% Traditional ROI: 3.02%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$520,000	Airbnb cash on cash: 5.77% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.77% Traditional ROI: 3.96%
648 ORANGE BELT LOOP Winter Garden, FL Welcome to your opportunity to own in one of the most desirable locations near downtown Wi...	3 beds \| 3 baths \| 1,688 sq.ft.	$499,990	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.37% Airbnb Rental Income: $1636 Traditional Rental Income: $2902 Airbnb ROI: -0.32% Traditional ROI: 3.37%
8256 BAYVIEW CROSSING DRIVE Winter Garden, FL Under contract-accepting backup offers. PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon...	4 beds \| 4 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 4.32% Airbnb Rental Income: $5064 Traditional Rental Income: $4693 Airbnb ROI: 3.27% Traditional ROI: 4.32%
634 FOSTER AVENUE Winter Garden, FL Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down ...	2 beds \| 1 baths \| 696 sq.ft.	$285,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 4.48% Airbnb Rental Income: $2340 Traditional Rental Income: $1916 Airbnb ROI: 3.9% Traditional ROI: 4.48%
14501 GROVE RESORT AVENUE #1727 Winter Garden, FL This luxurious 2-bedroom, 2-bath vacation condo is the ultimate retreat for those seeking ...	2 beds \| 2 baths \| 1,265 sq.ft.	$298,500	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.56% Airbnb Rental Income: $2340 Traditional Rental Income: $2582 Airbnb ROI: -0.36% Traditional ROI: 2.56%
131 OAK LAUREL DRIVE Winter Garden, FL 131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable ...	3 beds \| 4 baths \| 1,906 sq.ft.	$869,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 1.71% Airbnb Rental Income: $1636 Traditional Rental Income: $3797 Airbnb ROI: -1.53% Traditional ROI: 1.71%
15334 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL Beautiful 3-bedroom, 2.5-bathroom townhouse available in the great Summerlake community of...	3 beds \| 3 baths \| 1,868 sq.ft.	$450,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 3.86% Airbnb Rental Income: $1636 Traditional Rental Income: $3164 Airbnb ROI: -0.86% Traditional ROI: 3.86%
14501 GROVE RESORT AVENUE #3535 Winter Garden, FL GREAT OWNER FINANCING AVAILABLE: CONTACT US FOR ADDITIONAL INFORMATION. BEAUTIFUL 2 BED/2 ...	2 beds \| 2 baths \| 1,434 sq.ft.	$389,990	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.87% Airbnb Rental Income: $2340 Traditional Rental Income: $2808 Airbnb ROI: -0.99% Traditional ROI: 1.87%
14602 WINTER STAY DRIVE Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 4 baths \| 3,433 sq.ft.	$780,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 3.79% Airbnb Rental Income: $5064 Traditional Rental Income: $4427 Airbnb ROI: 3.25% Traditional ROI: 3.79%
14501 GROVE RESORT AVENUE #1440 Winter Garden, FL ust minutes from Disney, this fully furnished condo at The Grove Resort and Waterpark offe...	2 beds \| 2 baths \| 1,375 sq.ft.	$245,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2672 Airbnb ROI: -0.68% Traditional ROI: 3.26%
14501 GROVE RESORT AVENUE #2602 Winter Garden, FL Experience the best of both worlds with this incredible fully furnished 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,396 sq.ft.	$299,000	Airbnb cash on cash: -3.47% Traditional cash on cash: 1.87% Airbnb Rental Income: $1636 Traditional Rental Income: $2678 Airbnb ROI: -3.47% Traditional ROI: 1.87%
14501 GROVE RESORT AVENUE #2119 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	3 beds \| 2 baths \| 1,396 sq.ft.	$224,000	Airbnb cash on cash: -4.15% Traditional cash on cash: 2.9% Airbnb Rental Income: $1636 Traditional Rental Income: $2671 Airbnb ROI: -4.15% Traditional ROI: 2.9%
14501 GROVE RESORT AVENUE #3215 Winter Garden, FL Welcome to Grove Resort! Located on the second floor of Building 3, this unit is your laun...	2 beds \| 2 baths \| 1,265 sq.ft.	$239,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.69% Airbnb Rental Income: $2340 Traditional Rental Income: $2617 Airbnb ROI: -0.1% Traditional ROI: 3.69%
15508 BLACKBEAD STREET Winter Garden, FL One or more photo(s) has been virtually staged. If youâre looking for low-maintenance li...	3 beds \| 3 baths \| 1,754 sq.ft.	$430,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.64% Airbnb Rental Income: $1636 Traditional Rental Income: $2926 Airbnb ROI: -0.71% Traditional ROI: 3.64%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Winter Garden, FL

849 SHADOWMOSS DRIVE

Winter Garden, FL

5 beds | 3 baths | 2,620 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.48%

Airbnb Rental Income: $null

Traditional Rental Income: $3077

Airbnb ROI: N/A

Traditional ROI: 2.48%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

3 beds | 3 baths | 2,138 sq.ft.

$609,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1636

Traditional Rental Income: $3295

Airbnb ROI: -0.5%

Traditional ROI: 3.22%

15140 SUNRISE GROVE COURT

Winter Garden, FL

3 beds | 3 baths | 2,012 sq.ft.

$390,987

Airbnb cash on cash: -0.74%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1636

Traditional Rental Income: $3302

Airbnb ROI: -0.74%

Traditional ROI: 5.07%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

4 beds | 5 baths | 3,468 sq.ft.

$745,000

Airbnb cash on cash: 3.64%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $5980

Airbnb ROI: 3.64%

Traditional ROI: 6.44%

264 BLUE STONE CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,538 sq.ft.

$725,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $5064

Traditional Rental Income: $3698

Airbnb ROI: 4.02%

Traditional ROI: 3.53%

2202 ROMANUM DRIVE

Winter Garden, FL

3 beds | 2 baths | 1,889 sq.ft.

$585,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1636

Traditional Rental Income: $2435

Airbnb ROI: -0.1%

Traditional ROI: 2.21%

16232 ROCK COAST DRIVE

Winter Garden, FL

4 beds | 5 baths | 3,491 sq.ft.

$925,000

Airbnb cash on cash: 2.41%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $5064

Traditional Rental Income: $7312

Airbnb ROI: 2.41%

Traditional ROI: 6.22%

373 ERON WAY #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$163,999

Airbnb cash on cash: 5.44%

Traditional cash on cash: 6.23%

Airbnb Rental Income: $2340

Traditional Rental Income: $1885

Airbnb ROI: 5.44%