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.

Townhouses for Sale in Winter Garden, FL

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

Showing 73 Townhouse 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
14488 WHITTRIDGE DRIVE Winter Garden, FL Unique opportunity in highly desired Independence (Winter Garden)! This corner, end-unit t...	4 beds \| 3 baths \| 2,159 sq.ft.	$479,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 3.61% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 6.12% Traditional ROI: 3.61%
14815 DRIFTWATER DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. New Price! Discover this beautifully updat...	4 beds \| 3 baths \| 1,997 sq.ft.	$439,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 2.66% Airbnb Rental Income: $5064 Traditional Rental Income: $2686 Airbnb ROI: 5.93% Traditional ROI: 2.66%
8164 WOOD SAGE DRIVE Winter Garden, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirabl...	3 beds \| 3 baths \| 1,853 sq.ft.	$449,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.3% Airbnb Rental Income: $1636 Traditional Rental Income: $2668 Airbnb ROI: -0.24% Traditional ROI: 3.3%
900 WALKERS GROVE LANE Winter Garden, FL Welcome to 900 Walkers Grove Lane, a stunning home located in the desirable Downtown Winte...	3 beds \| 3 baths \| 1,905 sq.ft.	$489,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.26% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.12% Traditional ROI: 3.26%
1551 SCARLET OAK LOOP #B Winter Garden, FL Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION! Welcome to Tucker Oa...	3 beds \| 3 baths \| 1,422 sq.ft.	$329,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 4.77% Airbnb Rental Income: $1636 Traditional Rental Income: $2239 Airbnb ROI: 1.32% Traditional ROI: 4.77%
5755 NEW INDEPENDENCE PARKWAY Winter Garden, FL Under contract-accepting backup offers. Rare 4-bedroom, 2.5-bathroom townhome offering ove...	4 beds \| 3 baths \| 2,061 sq.ft.	$418,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 3.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2752 Airbnb ROI: 7.25% Traditional ROI: 3.98%
8919 Lakeshore Pointe Drive Winter Garden, FL This spacious 3-bedrooms , 3.5 bathrooms, Beautiful BONUS ROOM above the garage offers 2.5...	3 beds \| 3 baths \| 2,581 sq.ft.	$639,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 3% Airbnb Rental Income: $1636 Traditional Rental Income: $2987 Airbnb ROI: -0.04% Traditional ROI: 3%
1312 AZALEA WAY Winter Garden, FL Under contract-accepting backup offers. Located in the heart of Winter Garden, this 3 bedr...	3 beds \| 2 baths \| 1,216 sq.ft.	$265,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 4.88% Airbnb Rental Income: $1636 Traditional Rental Income: $1902 Airbnb ROI: 1.97% Traditional ROI: 4.88%
6578 CALAMONDIN DRIVE Winter Garden, FL Under contract-accepting backup offers. This luxury 4bd/3ba townhouse is located in the hi...	4 beds \| 3 baths \| 1,853 sq.ft.	$427,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 2.62% Airbnb Rental Income: $5064 Traditional Rental Income: $2616 Airbnb ROI: 6.16% Traditional ROI: 2.62%
14421 VASHONS WAY Winter Garden, FL Experience the best of Florida living just 20 minutes from Disney! This move-in ready 2 be...	2 beds \| 3 baths \| 1,088 sq.ft.	$359,900	Airbnb cash on cash: 2.27% Traditional cash on cash: 3.04% Airbnb Rental Income: $2340 Traditional Rental Income: $2020 Airbnb ROI: 2.27% Traditional ROI: 3.04%
149 S PARK AVENUE Winter Garden, FL Gorgeous former model in this beautiful masonry wrapped complex in the heart of Winter Gar...	3 beds \| 4 baths \| 2,938 sq.ft.	$1,049,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 1.06% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.71% Traditional ROI: 1.06%
428 SAND LIME ROAD Winter Garden, FL Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, 3 bedroom, 1.5 bath townhome ...	3 beds \| 2 baths \| 1,234 sq.ft.	$225,000	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%
1350 WINTER GREEN WAY Winter Garden, FL Simply Perfect Home or Investment Opportunity in Winter Garden! Welcome to 1350 Winter Gr...	2 beds \| 2 baths \| 1,190 sq.ft.	$274,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 4.47% Airbnb Rental Income: $2340 Traditional Rental Income: $1795 Airbnb ROI: 4.34% Traditional ROI: 4.47%
11032 Great Rock Street Winter Garden, FL The Ibis at Waterleigh is a spacious town home with 3 bedrooms, 2.5 baths with stainless s...	3 beds \| 3 baths \| 1,567 sq.ft.	$419,900	Airbnb cash on cash: 0.3% Traditional cash on cash: 3.53% Airbnb Rental Income: $1636 Traditional Rental Income: $2447 Airbnb ROI: 0.3% Traditional ROI: 3.53%
11018 HANLON TERRACE ALLEY Winter Garden, FL Beautiful 2019 built townhome located in sought after Winding Bay Preserve. Located just 1...	4 beds \| 3 baths \| 2,037 sq.ft.	$425,000	Airbnb cash on cash: 6.88% Traditional cash on cash: 4.14% Airbnb Rental Income: $5064 Traditional Rental Income: $2937 Airbnb ROI: 6.88% Traditional ROI: 4.14%
9814 AMBER CHESTNUT WAY Winter Garden, FL Expect to be impressed with this 4BR home in the desirable Watermark community. Room for e...	4 beds \| 4 baths \| 2,303 sq.ft.	$465,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 3.63% Airbnb Rental Income: $5064 Traditional Rental Income: $3218 Airbnb ROI: 5.5% Traditional ROI: 3.63%
15975 MARINA BAY DRIVE Winter Garden, FL PRICE REDUCED! This light and airy end-unit townhome is located in the sought-after Hawksm...	3 beds \| 3 baths \| 2,070 sq.ft.	$484,999	Airbnb cash on cash: -0.74% Traditional cash on cash: 3.28% Airbnb Rental Income: $1636 Traditional Rental Income: $2995 Airbnb ROI: -0.74% Traditional ROI: 3.28%
16333 INGRAM HILLS ALY Winter Garden, FL SELLER IS MOTIVATED! This former model, 2024 corner townhome, offers 3 bedrooms, 2.5 bathr...	3 beds \| 3 baths \| 1,644 sq.ft.	$448,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.29% Airbnb Rental Income: $1636 Traditional Rental Income: $2653 Airbnb ROI: 0.77% Traditional ROI: 4.29%
14971 APOLLO BOND DRIVE Winter Garden, FL This luxurious townhouse, built in 2019, is located in the Watermark Community in Horizon ...	3 beds \| 3 baths \| 1,655 sq.ft.	$448,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.46% Airbnb Rental Income: $1636 Traditional Rental Income: $2360 Airbnb ROI: -0.37% Traditional ROI: 2.46%
5718 CYPRESS HILL ROAD Winter Garden, FL Welcome to Your Dream Townhome in Orchard Hills This stunning townhome in the heart of ...	3 beds \| 3 baths \| 1,712 sq.ft.	$445,990	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.84% Airbnb Rental Income: $1636 Traditional Rental Income: $2423 Airbnb ROI: -0.15% Traditional ROI: 2.84%
6560 CANDIED PEEL ALLEY Winter Garden, FL BEAUTIFUL 4 bedrooms and 3 bathrooms townhouse located in new Winter Garden area, the kit...	4 beds \| 4 baths \| 1,902 sq.ft.	$430,000	Airbnb cash on cash: 6.33% Traditional cash on cash: 4.1% Airbnb Rental Income: $5064 Traditional Rental Income: $3136 Airbnb ROI: 6.33% Traditional ROI: 4.1%
6572 CALAMONDIN DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to Hamlin Reserve, where location ...	3 beds \| 3 baths \| 1,908 sq.ft.	$449,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 3.41% Airbnb Rental Income: $1636 Traditional Rental Income: $2739 Airbnb ROI: -0.31% Traditional ROI: 3.41%
9736 AMBER CHESTNUT WAY Winter Garden, FL Welcome to this beautifully appointed 4 bedroom, 2.5 bath end unit townhome with a front p...	4 beds \| 3 baths \| 1,937 sq.ft.	$449,900	Airbnb cash on cash: 6.75% Traditional cash on cash: 3.6% Airbnb Rental Income: $5064 Traditional Rental Income: $2702 Airbnb ROI: 6.75% Traditional ROI: 3.6%
765 WALKERS GROVE LANE Winter Garden, FL Luxury Townhome in Walkers Grove â Winter Gardenâs Finest Living Welcome to this st...	3 beds \| 3 baths \| 1,866 sq.ft.	$520,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.04% Airbnb Rental Income: $1636 Traditional Rental Income: $2638 Airbnb ROI: 0.02% Traditional ROI: 3.04%
12043 HOLYSTONE STREET Winter Garden, FL âThe property is currently active for sale but is rented for $2500 monthly, with a lease...	3 beds \| 3 baths \| 1,568 sq.ft.	$399,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 2.83% Airbnb Rental Income: $1636 Traditional Rental Income: $2390 Airbnb ROI: -0.42% Traditional ROI: 2.83%
13809 LUNA HARVEST AVENUE Winter Garden, FL Luxurious new townhome by RockWell Homes features a covered front patio, back lanai, two p...	3 beds \| 3 baths \| 1,785 sq.ft.	$440,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.86% Airbnb Rental Income: $1636 Traditional Rental Income: $2625 Airbnb ROI: 0.34% Traditional ROI: 3.86%
10400 Spring Arbor Lane Winter Garden, FL Welcome to this beautifully updated townhouse in the highly desirable Winding Bay Preserve...	3 beds \| 3 baths \| 1,868 sq.ft.	$429,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 3.73% Airbnb Rental Income: $1636 Traditional Rental Income: $2760 Airbnb ROI: -0.21% Traditional ROI: 3.73%
13528 AUTUMN HARVEST AVENUE Winter Garden, FL New Luxurious Townhome by RockWell Homes. Welcome to this exquisite new Edison townhome w...	3 beds \| 3 baths \| 1,955 sq.ft.	$490,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.71% Airbnb Rental Income: $1636 Traditional Rental Income: $2781 Airbnb ROI: 0.2% Traditional ROI: 3.71%
13536 AUTUMN HARVEST AVENUE Winter Garden, FL Luxurious new townhome by RockWell Homes offers a stunning blend of elegance and functiona...	3 beds \| 3 baths \| 1,785 sq.ft.	$470,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 3.54% Airbnb Rental Income: $1636 Traditional Rental Income: $2621 Airbnb ROI: 0.25% Traditional ROI: 3.54%
16518 BROOK SPRINGS ALLEY Winter Garden, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 3 baths \| 1,568 sq.ft.	$380,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 4.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2408 Airbnb ROI: 0.56% Traditional ROI: 4.02%
963 STUCKI TERRACE Winter Garden, FL *** Price Improvement! Cozy Townhome Just Minutes from Downtown Winter Garden. Discover co...	2 beds \| 1 baths \| 761 sq.ft.	$199,900	Airbnb cash on cash: 6.28% Traditional cash on cash: 5.39% Airbnb Rental Income: $2340 Traditional Rental Income: $1592 Airbnb ROI: 6.28% Traditional ROI: 5.39%
1122 PRIORY CIRCLE Winter Garden, FL Great Opportunity to buy a CORNER LOT and immaculate 2 story town home in the Stoneybrook ...	3 beds \| 3 baths \| 1,748 sq.ft.	$384,990	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.84% Airbnb Rental Income: $1636 Traditional Rental Income: $2380 Airbnb ROI: -0.5% Traditional ROI: 2.84%
13452 SAGESTONE DRIVE Winter Garden, FL Discover this stunning corner-unit townhouse in the highly desirable Waterleigh community ...	3 beds \| 3 baths \| 1,814 sq.ft.	$479,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 2.66% Airbnb Rental Income: $1636 Traditional Rental Income: $2643 Airbnb ROI: -0.62% Traditional ROI: 2.66%
9591 AMBER CHESTNUT WAY Winter Garden, FL Step into stylish, low-maintenance luxury in this beautifully maintained townhome nestled ...	3 beds \| 3 baths \| 1,789 sq.ft.	$450,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.22% Airbnb Rental Income: $1636 Traditional Rental Income: $2629 Airbnb ROI: -0.23% Traditional ROI: 3.22%
14897 EVERGREEN OAK LOOP Winter Garden, FL **This property qualifies for a closing cost credit up to $6,300 through the Sellerâs pr...	3 beds \| 3 baths \| 1,748 sq.ft.	$414,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.19% Airbnb Rental Income: $1636 Traditional Rental Income: $2463 Airbnb ROI: -0.13% Traditional ROI: 3.19%
9368 BOLSHOI ALLEY Winter Garden, FL Under Construction. Welcome to 9368 Bolshoi Alley in Winter Garden, a stunning new constru...	3 beds \| 3 baths \| 1,833 sq.ft.	$457,990	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.82% Airbnb Rental Income: $1636 Traditional Rental Income: $2650 Airbnb ROI: 0.38% Traditional ROI: 3.82%
9380 BOLSHOI ALLEY Winter Garden, FL Under Construction. Welcome to 9380 Bolshoi Alley in Winter Garden, Florida, a stunning ne...	3 beds \| 3 baths \| 1,691 sq.ft.	$427,990	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.74% Airbnb Rental Income: $1636 Traditional Rental Income: $2485 Airbnb ROI: 0.47% Traditional ROI: 3.74%
1010 STUCKI TERRACE Winter Garden, FL Westside Townhomes One story unit with 3 bedrooms and 2 full baths Covered screened ...	3 beds \| 2 baths \| 984 sq.ft.	$229,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 5.42% Airbnb Rental Income: $1636 Traditional Rental Income: $1760 Airbnb ROI: 2.73% Traditional ROI: 5.42%
13166 CALMING BREEZE WAY Winter Garden, FL One or more photo(s) has been virtually staged. Under Construction. Images shown are for i...	3 beds \| 3 baths \| 1,715 sq.ft.	$436,080	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.26% Airbnb Rental Income: $1636 Traditional Rental Income: $2436 Airbnb ROI: 0.17% Traditional ROI: 3.26%
15471 HONEYBELL DRIVE Winter Garden, FL MAJOR PRICE REDUCTION! Welcome to 15471 Honeybell Drive, a beautifully designed home in th...	3 beds \| 3 baths \| 1,584 sq.ft.	$389,990	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.66% Airbnb Rental Income: $1636 Traditional Rental Income: $2392 Airbnb ROI: -0.67% Traditional ROI: 2.66%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Garden, FL

14488 WHITTRIDGE DRIVE

Winter Garden, FL

4 beds | 3 baths | 2,159 sq.ft.

$479,000

Airbnb cash on cash: 6.12%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $5064

Traditional Rental Income: $2907

Airbnb ROI: 6.12%

Traditional ROI: 3.61%

14815 DRIFTWATER DRIVE

Winter Garden, FL

4 beds | 3 baths | 1,997 sq.ft.

$439,000

Airbnb cash on cash: 5.93%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $5064

Traditional Rental Income: $2686

Airbnb ROI: 5.93%

Traditional ROI: 2.66%

8164 WOOD SAGE DRIVE

Winter Garden, FL

3 beds | 3 baths | 1,853 sq.ft.

$449,900

Airbnb cash on cash: -0.24%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1636

Traditional Rental Income: $2668

Airbnb ROI: -0.24%

Traditional ROI: 3.3%

900 WALKERS GROVE LANE

Winter Garden, FL

3 beds | 3 baths | 1,905 sq.ft.

$489,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $1636

Traditional Rental Income: $2723

Airbnb ROI: -0.12%

Traditional ROI: 3.26%

1551 SCARLET OAK LOOP #B

Winter Garden, FL

3 beds | 3 baths | 1,422 sq.ft.

$329,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1636

Traditional Rental Income: $2239

Airbnb ROI: 1.32%

Traditional ROI: 4.77%

5755 NEW INDEPENDENCE PARKWAY

Winter Garden, FL

4 beds | 3 baths | 2,061 sq.ft.

$418,000

Airbnb cash on cash: 7.25%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $5064

Traditional Rental Income: $2752

Airbnb ROI: 7.25%

Traditional ROI: 3.98%

8919 Lakeshore Pointe Drive

Winter Garden, FL

3 beds | 3 baths | 2,581 sq.ft.

$639,900

Airbnb cash on cash: -0.04%

Traditional cash on cash: 3%

Airbnb Rental Income: $1636

Traditional Rental Income: $2987

Airbnb ROI: -0.04%

Traditional ROI: 3%

1312 AZALEA WAY

Winter Garden, FL

3 beds | 2 baths | 1,216 sq.ft.

$265,000

Airbnb cash on cash: 1.97%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1636

Traditional Rental Income: $1902

Airbnb ROI: 1.97%