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.

Woodlawn Investment Property for Sale in Winter Garden, FL

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

Showing 898 Woodlawn 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
607 E Oakland Ave Winter Garden, FL Welcome to this exceptional Winter Garden home with 4 bedrooms, 3.5-bathrooms, PLUS home o...	4 beds \| 3 baths \| 3,406 sq.ft.	$865,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.99% Airbnb Rental Income: $5064 Traditional Rental Income: $4139 Airbnb ROI: 2.86% Traditional ROI: 2.99%
7189 Summerlake Groves St Winter Garden, FL COME set your eyes on this Gorgeous 2-Story Winter Garden home located in Highlands at Sum...	3 beds \| 2 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.51% Airbnb Rental Income: $1636 Traditional Rental Income: $2922 Airbnb ROI: -0.51% Traditional ROI: 2.51%
14372 Sunbridge Cir Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 4 baths \| 3,468 sq.ft.	$775,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 5.68% Airbnb Rental Income: $5064 Traditional Rental Income: $5780 Airbnb ROI: 3.33% Traditional ROI: 5.68%
14046 Fox Glove St Winter Garden, FL Stunning golf course frontage home in the highly desirable Stoneybrook West gated communit...	4 beds \| 3 baths \| 2,970 sq.ft.	$755,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3329 Airbnb ROI: N/A Traditional ROI: 2.61%
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: 5.22% Traditional cash on cash: 4.64% Airbnb Rental Income: $2340 Traditional Rental Income: $1667 Airbnb ROI: 5.22% Traditional ROI: 4.64%
14501 Grove Resort Ave #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: -0.54% Traditional cash on cash: 1.18% Airbnb Rental Income: $2340 Traditional Rental Income: $2110 Airbnb ROI: -0.54% Traditional ROI: 1.18%
714 Parkmont Pl Winter Garden, FL Welcome to the GOLF CART district of WINTER GARDEN! This STUNNING home was the former Ryan...	3 beds \| 2 baths \| 2,190 sq.ft.	$549,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.35% Airbnb Rental Income: $1636 Traditional Rental Income: $2588 Airbnb ROI: -0.31% Traditional ROI: 2.35%
14282 Creekbed Cir Winter Garden, FL Price improvement and quick close available. WELCOME HOME: YOUR WINTER GARDEN ESCAPE AWAI...	4 beds \| 4 baths \| 3,479 sq.ft.	$929,500	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.44% Airbnb Rental Income: $5064 Traditional Rental Income: $4828 Airbnb ROI: 2.52% Traditional ROI: 3.44%
14645 Scott Key Dr Winter Garden, FL Beautifully updated single-family home featuring NEW EXTERIOR PAINT AND NEW FLOORING THROU...	4 beds \| 3 baths \| 3,427 sq.ft.	$890,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.81% Airbnb Rental Income: $5064 Traditional Rental Income: $3797 Airbnb ROI: 2.07% Traditional ROI: 1.81%
14801 Evergreen Oak Loop Winter Garden, FL Welcome to Your Dream Townhome! Perfectly situated on a desirable corner lot, this charmi...	3 beds \| 2 baths \| 1,741 sq.ft.	$399,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.72% Airbnb Rental Income: $1636 Traditional Rental Income: $2512 Airbnb ROI: -0.72% Traditional ROI: 2.72%
900 Walkers Grove Ln Winter Garden, FL Downtown Winter Garden â Golf Cart District! Donât miss this amazing opportunity to...	3 beds \| 2 baths \| 1,905 sq.ft.	$490,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.17% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.14% Traditional ROI: 3.17%
14095 Title Way Winter Garden, FL Welcome to this move-in-ready townhome in the heart of Winter Gardenâs highly sought-aft...	3 beds \| 2 baths \| 1,628 sq.ft.	$440,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 3% Airbnb Rental Income: $1636 Traditional Rental Income: $2648 Airbnb ROI: -0.49% Traditional ROI: 3%
14501 Grove Resort Ave #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: 0.48% Airbnb Rental Income: $1636 Traditional Rental Income: $2171 Airbnb ROI: -2.56% Traditional ROI: 0.48%
15852 Shorebird Ln Winter Garden, FL Stunning 2-Story Home in Winter Garden â 4 Bedrooms, Solar Panels, and Exceptional Featu...	4 beds \| 4 baths \| 2,766 sq.ft.	$829,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.78% Airbnb Rental Income: $5064 Traditional Rental Income: $3857 Airbnb ROI: 1.99% Traditional ROI: 1.78%
15372 Gilligan Ct Winter Garden, FL Stunning One-Story Home in the Heart of Horizon West â Beautifully Renovated and Move-In...	4 beds \| 3 baths \| 2,781 sq.ft.	$870,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3697 Airbnb ROI: 2.75% Traditional ROI: 2.34%
5531 Cypress Hill Rd Winter Garden, FL Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills...	4 beds \| 3 baths \| 2,204 sq.ft.	$625,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $2827 Airbnb ROI: 4.02% Traditional ROI: 1.96%
8256 Bayview Crossing Dr Winter Garden, FL PRICE IMPROVEMENT....UPGRADED POOL HOME in Horizon West! Welcome to this 4-bed, 3.5-bath,...	4 beds \| 3 baths \| 2,557 sq.ft.	$675,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3546 Airbnb ROI: 3.27% Traditional ROI: 2.5%
634 Foster Ave 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: 2.86% Airbnb Rental Income: $2340 Traditional Rental Income: $1483 Airbnb ROI: 3.9% Traditional ROI: 2.86%
14501 Grove Resort Ave #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: 1.66% Airbnb Rental Income: $2340 Traditional Rental Income: $2327 Airbnb ROI: -0.36% Traditional ROI: 1.66%
131 Oak Laurel Dr Winter Garden, FL 131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable ...	3 beds \| 3 baths \| 1,906 sq.ft.	$895,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 1% Airbnb Rental Income: $1636 Traditional Rental Income: $3266 Airbnb ROI: -1.51% Traditional ROI: 1%
14501 Grove Resort Ave #1617 Winter Garden, FL Complete turnkey unit with prime views to the lake, pool and Disney parks area. One of the...	2 beds \| 2 baths \| 1,375 sq.ft.	$450,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.96% Airbnb Rental Income: $2340 Traditional Rental Income: $2545 Airbnb ROI: -0.9% Traditional ROI: 0.96%
14501 Grove Resort Ave #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: 0.19% Airbnb Rental Income: $2340 Traditional Rental Income: $2193 Airbnb ROI: -0.99% Traditional ROI: 0.19%
14602 Winter Stay Dr Winter Garden, FL Fantastic opportunity to own this exceptional home in the highly sought-after WATERMARK co...	4 beds \| 3 baths \| 3,433 sq.ft.	$780,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 3.24% Airbnb Rental Income: $5064 Traditional Rental Income: $4026 Airbnb ROI: 3.25% Traditional ROI: 3.24%
16253 Pebble Bluff Loop Winter Garden, FL Currently house has a tenant - opportunity for investors Waterleigh is a resort-s...	3 beds \| 2 baths \| 1,700 sq.ft.	$476,900	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.06% Airbnb Rental Income: $1636 Traditional Rental Income: $2332 Airbnb ROI: -0.54% Traditional ROI: 2.06%
17661 Davenport Rd Winter Garden, FL Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural ...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,125,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.03% Airbnb Rental Income: $1636 Traditional Rental Income: $5347 Airbnb ROI: -0.79% Traditional ROI: 3.03%
14501 Grove Resort Ave #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: -0.72% Traditional cash on cash: 1.57% Airbnb Rental Income: $2340 Traditional Rental Income: $2362 Airbnb ROI: -0.72% Traditional ROI: 1.57%
14501 Grove Resort Ave #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: 0.08% Airbnb Rental Income: $1636 Traditional Rental Income: $2174 Airbnb ROI: -3.47% Traditional ROI: 0.08%
14501 Grove Resort Ave #2119 Winter Garden, FL Gorgeous Lakeview Condo at The Grove Resort & Water Park Orlando! Perfect for snowbirds o...	3 beds \| 2 baths \| 1,396 sq.ft.	$224,000	Airbnb cash on cash: -3.54% Traditional cash on cash: 0.5% Airbnb Rental Income: $1636 Traditional Rental Income: $2238 Airbnb ROI: -3.54% Traditional ROI: 0.5%
14501 Grove Resort Ave #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: -0.14% Traditional cash on cash: 1.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2089 Airbnb ROI: -0.14% Traditional ROI: 1.26%
15508 Blackbead St Winter Garden, FL One or more photo(s) has been virtually staged. If youâre looking for low-maintenance li...	3 beds \| 2 baths \| 1,754 sq.ft.	$440,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.5% Airbnb Rental Income: $1636 Traditional Rental Income: $2515 Airbnb ROI: -0.72% Traditional ROI: 2.5%
14501 Grove Resort Ave #3406 Winter Garden, FL Gorgeous Lakeview Condo at The Grove Resort & Water Park Orlando! Perfect for snowbirds o...	2 beds \| 2 baths \| 1,265 sq.ft.	$204,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 1.38% Airbnb Rental Income: $2340 Traditional Rental Income: $2194 Airbnb ROI: -0.29% Traditional ROI: 1.38%
14501 Grove Resort Ave #1220 Winter Garden, FL Great Location â Steps from Resort Amenities at The Grove! Enjoy the ultimate Orlando v...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.43% Airbnb Rental Income: $2340 Traditional Rental Income: $2255 Airbnb ROI: -0.18% Traditional ROI: 1.43%
15058 Sawgrass Bluff Dr Winter Garden, FL Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjac...	4 beds \| 2 baths \| 2,626 sq.ft.	$600,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3031 Airbnb ROI: 4.72% Traditional ROI: 2.93%
428 Sand Lime Rd Winter Garden, FL Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, 3 bedroom, 1.5 bath townhome ...	3 beds \| 1 baths \| 1,234 sq.ft.	$220,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 6.2% Airbnb Rental Income: $1636 Traditional Rental Income: $1901 Airbnb ROI: 2.79% Traditional ROI: 6.2%
16125 Azure Key St Winter Garden, FL Welcome home to the highly sought-after Waterleigh community in Horizon West. This bright ...	3 beds \| 2 baths \| 1,685 sq.ft.	$480,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 4.27% Airbnb Rental Income: $1636 Traditional Rental Income: $3377 Airbnb ROI: -0.53% Traditional ROI: 4.27%
5637 Water Rose Rd Winter Garden, FL Welcome to this beautifully maintained townhome located in the highly desirable Independen...	3 beds \| 2 baths \| 1,617 sq.ft.	$419,990	Airbnb cash on cash: -0.73% Traditional cash on cash: 2.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2397 Airbnb ROI: -0.73% Traditional ROI: 2.24%
1534 E Spring Ridge Cir Winter Garden, FL Welcome to this stunning updated 3-bedroom, 2-bath home located in one of Winter Gardenâ...	3 beds \| 2 baths \| 1,688 sq.ft.	$554,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.1% Airbnb Rental Income: $1636 Traditional Rental Income: $2709 Airbnb ROI: 0.14% Traditional ROI: 3.1%
11032 Great Rock St Winter Garden, FL The Ibis at Waterleigh is a spacious town home with 3 bedrooms, 2.5 baths with stainless s...	3 beds \| 2 baths \| 1,567 sq.ft.	$409,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $1636 Traditional Rental Income: $2447 Airbnb ROI: 0.33% Traditional ROI: 3.64%
500 Teacup Springs Ct Winter Garden, FL Short Sale. An exceptional opportunity for investors, builders, and developersâthis prop...	4 beds \| 3 baths \| 2,397 sq.ft.	$530,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.83% Airbnb Rental Income: $5064 Traditional Rental Income: $3060 Airbnb ROI: 5.79% Traditional ROI: 3.83%
14501 Grove Resort Ave #1622 Winter Garden, FL BEST VIEW IN THE ENTIRE RESORT! This is the largest condo offered at The Grove Resort & W...	3 beds \| 3 baths \| 1,544 sq.ft.	$449,000	Airbnb cash on cash: -2.24% Traditional cash on cash: 1.31% Airbnb Rental Income: $1636 Traditional Rental Income: $2666 Airbnb ROI: -2.24% Traditional ROI: 1.31%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Winter Garden, FL

607 E Oakland Ave

Winter Garden, FL

4 beds | 3 baths | 3,406 sq.ft.

$865,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $5064

Traditional Rental Income: $4139

Airbnb ROI: 2.86%

Traditional ROI: 2.99%

7189 Summerlake Groves St

Winter Garden, FL

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

$609,999

Airbnb cash on cash: -0.51%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1636

Traditional Rental Income: $2922

Airbnb ROI: -0.51%

Traditional ROI: 2.51%

14372 Sunbridge Cir

Winter Garden, FL

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

$775,000

Airbnb cash on cash: 3.33%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $5064

Traditional Rental Income: $5780

Airbnb ROI: 3.33%

Traditional ROI: 5.68%

14046 Fox Glove St

Winter Garden, FL

4 beds | 3 baths | 2,970 sq.ft.

$755,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3329

Airbnb ROI: N/A

Traditional ROI: 2.61%

373 Eron Way #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$163,999

Airbnb cash on cash: 5.22%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2340

Traditional Rental Income: $1667

Airbnb ROI: 5.22%

Traditional ROI: 4.64%

14501 Grove Resort Ave #1111

Winter Garden, FL

2 beds | 2 baths | 1,265 sq.ft.

$205,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $2340

Traditional Rental Income: $2110

Airbnb ROI: -0.54%

Traditional ROI: 1.18%

714 Parkmont Pl

Winter Garden, FL

3 beds | 2 baths | 2,190 sq.ft.

$549,900

Airbnb cash on cash: -0.31%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $1636

Traditional Rental Income: $2588

Airbnb ROI: -0.31%

Traditional ROI: 2.35%

14282 Creekbed Cir

Winter Garden, FL

4 beds | 4 baths | 3,479 sq.ft.

$929,500

Airbnb cash on cash: 2.52%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $4828

Airbnb ROI: 2.52%