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 56 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
1424 SCARLET OAK Loop Winter Garden, FL Welcome to your beautifully updated home in the gated community of Winter Garden. This cha...	3 beds \| 3 baths \| 1,737 sq.ft.	$379,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 4.56% Airbnb Rental Income: $1303 Traditional Rental Income: $2544 Airbnb ROI: -0.07% Traditional ROI: 4.56%
760 WALKERS GROVE Lane Winter Garden, FL WELCOME HOME to this immaculately maintained 3-bedroom, 2.5-bath townhome with a 2-car gar...	3 beds \| 3 baths \| 1,915 sq.ft.	$540,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 2.99% Airbnb Rental Income: $1303 Traditional Rental Income: $2695 Airbnb ROI: -0.58% Traditional ROI: 2.99%
8873 FOUNTAIN PALM Alley Winter Garden, FL Luxury Toll Brothers End-Unit Townhome in Lakeshore Preserve! This beautifully maintained ...	3 beds \| 3 baths \| 2,162 sq.ft.	$565,000	Airbnb cash on cash: -1.95% Traditional cash on cash: 2.54% Airbnb Rental Income: $1303 Traditional Rental Income: $3264 Airbnb ROI: -1.95% Traditional ROI: 2.54%
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.	$799,000	Airbnb cash on cash: -1.95% Traditional cash on cash: 1.95% Airbnb Rental Income: $1303 Traditional Rental Income: $3797 Airbnb ROI: -1.95% Traditional ROI: 1.95%
10509 SPRING ARBOR Lane Winter Garden, FL Seller is motivated! Take advantage of this incredible opportunity to own a beautifully ma...	3 beds \| 3 baths \| 1,868 sq.ft.	$439,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 2.91% Airbnb Rental Income: $1303 Traditional Rental Income: $2686 Airbnb ROI: -1.44% Traditional ROI: 2.91%
11025 SUSPENSE Drive Winter Garden, FL PRICE ENHANCEMENT + CHOOSE YOUR CABINET COLOR! Buyers who enter into an accepted contract ...	3 beds \| 3 baths \| 1,636 sq.ft.	$410,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.45% Airbnb Rental Income: $1303 Traditional Rental Income: $2591 Airbnb ROI: -0.96% Traditional ROI: 3.45%
5618 WATER ROSE Road Winter Garden, FL Seller is motivated!! This two-story townhome consists of three bedrooms, two and a half b...	3 beds \| 3 baths \| 1,755 sq.ft.	$375,000	Airbnb cash on cash: -2.1% Traditional cash on cash: 3.16% Airbnb Rental Income: $1303 Traditional Rental Income: $2749 Airbnb ROI: -2.1% Traditional ROI: 3.16%
8878 BISMARCK PALM Drive Winter Garden, FL PRICE IMPROVEMENT! Welcome to a beautifully upgraded residence in Lakeshore Preserve, one ...	4 beds \| 4 baths \| 2,581 sq.ft.	$629,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 2.07% Airbnb Rental Income: $4271 Traditional Rental Income: $3376 Airbnb ROI: 2.06% Traditional ROI: 2.07%
8866 BISMARCK PALM Drive Winter Garden, FL Luxury living in the ENZO Model townhome located in Lakeshore Preserve, a Toll Brothers co...	5 beds \| 4 baths \| 3,174 sq.ft.	$795,000	Airbnb cash on cash: -1.89% Traditional cash on cash: 2.26% Airbnb Rental Income: $1240 Traditional Rental Income: $3923 Airbnb ROI: -1.89% Traditional ROI: 2.26%
15877 TOLLINGTON Alley Winter Garden, FL Welcome to this beautiful end-unit townhome in the desirable Encore at Ovation community. ...	3 beds \| 3 baths \| 1,835 sq.ft.	$493,500	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.62% Airbnb Rental Income: $1303 Traditional Rental Income: $2668 Airbnb ROI: -0.22% Traditional ROI: 3.62%
14448 PLEACH Street Winter Garden, FL Welcome to this charming and spacious 2-bedroom, 2.5-bath town-home located in the highly ...	2 beds \| 3 baths \| 1,345 sq.ft.	$350,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.66% Airbnb Rental Income: $1522 Traditional Rental Income: $2138 Airbnb ROI: -0.56% Traditional ROI: 2.66%
15511 CAMPDEN Street Winter Garden, FL Located in the Stoneybrook West area of Winter Garden. Large townhouse offering 3 bedrooms...	3 beds \| 3 baths \| 1,916 sq.ft.	$369,900	Airbnb cash on cash: -1.33% Traditional cash on cash: 4.13% Airbnb Rental Income: $1303 Traditional Rental Income: $2791 Airbnb ROI: -1.33% Traditional ROI: 4.13%
17723 JAPONICA BLOOM Drive Winter Garden, FL BACK ON THE MARKET AND PRICED TO SELL!! Why wait for new construction when this move-in-re...	3 beds \| 3 baths \| 1,584 sq.ft.	$399,999	Airbnb cash on cash: -1.14% Traditional cash on cash: 1.8% Airbnb Rental Income: $1303 Traditional Rental Income: $2002 Airbnb ROI: -1.14% Traditional ROI: 1.8%
6982 TWILIGHT BAY Drive Winter Garden, FL Welcome to 6982 Twilight Bay Drive, a beautifully maintained two-story townhome located in...	4 beds \| 3 baths \| 1,860 sq.ft.	$475,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.96% Airbnb Rental Income: $4271 Traditional Rental Income: $3110 Airbnb ROI: 4.54% Traditional ROI: 3.96%
16425 PRAIRIE SCHOOL Drive Winter Garden, FL MOTIVATED SELLERS! Receive a $5,000 seller incentive that may be applied toward closing co...	3 beds \| 3 baths \| 1,662 sq.ft.	$414,900	Airbnb cash on cash: -1.34% Traditional cash on cash: 3.81% Airbnb Rental Income: $1303 Traditional Rental Income: $2901 Airbnb ROI: -1.34% Traditional ROI: 3.81%
8113 RED STOPPER Lane Winter Garden, FL Perfectly positioned in the heartbeat of Horizons West, just 3 miles from Disney's Magic K...	3 beds \| 3 baths \| 1,725 sq.ft.	$434,900	Airbnb cash on cash: -0.86% Traditional cash on cash: 4.13% Airbnb Rental Income: $1303 Traditional Rental Income: $2930 Airbnb ROI: -0.86% Traditional ROI: 4.13%
5413 NEW INDEPENDENCE Parkway Winter Garden, FL Beautiful 4-bedroom, 2.5-bathroom townhouse located in the desirable Winter Garden area. T...	4 beds \| 3 baths \| 2,131 sq.ft.	$488,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.72% Airbnb Rental Income: $4271 Traditional Rental Income: $3198 Airbnb ROI: 4.09% Traditional ROI: 3.72%
8012 BLUEJACK OAK Drive Winter Garden, FL Wake up to serene pond views and end your evenings watching the magic of fireworks light u...	4 beds \| 4 baths \| 2,222 sq.ft.	$479,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 4.56% Airbnb Rental Income: $4271 Traditional Rental Income: $3684 Airbnb ROI: 3.86% Traditional ROI: 4.56%
12003 HOLYSTONE Street Winter Garden, FL Welcome to Waterleigh-one of Winter Garden's most sought-after communities! This beautiful...	3 beds \| 3 baths \| 1,814 sq.ft.	$430,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.37% Airbnb Rental Income: $1303 Traditional Rental Income: $2642 Airbnb ROI: -0.96% Traditional ROI: 3.37%
7030 TWILIGHT BAY Drive Winter Garden, FL Short Sale. Great home, great shape, let's talk	4 beds \| 4 baths \| 1,920 sq.ft.	$469,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 4.1% Airbnb Rental Income: $4271 Traditional Rental Income: $3151 Airbnb ROI: 4.6% Traditional ROI: 4.1%
6131 ELFIN HERB Way Winter Garden, FL Welcome to 6131 Elfin Herb Way, a beautifully maintained home offering comfort, functional...	3 beds \| 3 baths \| 1,714 sq.ft.	$435,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 2.74% Airbnb Rental Income: $1303 Traditional Rental Income: $2495 Airbnb ROI: -1.18% Traditional ROI: 2.74%
13232 DANIELS LANDING Circle Winter Garden, FL Welcome to this beautifully maintained unfurnished 2-story townhouse located in the gated ...	2 beds \| 3 baths \| 1,232 sq.ft.	$325,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.08% Airbnb Rental Income: $1522 Traditional Rental Income: $2088 Airbnb ROI: -0.22% Traditional ROI: 3.08%
8937 LAKESHORE POINTE Drive Winter Garden, FL Stunning Luxury Townhome in Highly Sought-After Lakeshore Community! Welcome to this beaut...	3 beds \| 3 baths \| 2,052 sq.ft.	$585,000	Airbnb cash on cash: -1.75% Traditional cash on cash: 1.99% Airbnb Rental Income: $1303 Traditional Rental Income: $2938 Airbnb ROI: -1.75% Traditional ROI: 1.99%
9991 SCHROEDER Alley Winter Garden, FL Some photos are virtually staged. Video Tour Available. SELLER IS OFFERING A $5,000 CLOS...	3 beds \| 3 baths \| 1,568 sq.ft.	$384,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.41% Airbnb Rental Income: $1303 Traditional Rental Income: $2382 Airbnb ROI: -0.71% Traditional ROI: 3.41%
14942 WINDFLOWER Alley Winter Garden, FL Step into this beautifully designed 3-bedroom, 2.5-bath townhome located in the highly des...	3 beds \| 3 baths \| 1,536 sq.ft.	$405,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.99% Airbnb Rental Income: $1303 Traditional Rental Income: $2374 Airbnb ROI: -0.9% Traditional ROI: 2.99%
14014 SCARLET ASTER Alley Winter Garden, FL *** PRICE REDUCED *** Rare Dual Owner's Suite Townhome - Priced to Move, Near Disney T...	3 beds \| 3 baths \| 1,808 sq.ft.	$455,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.55% Airbnb Rental Income: $1303 Traditional Rental Income: $2584 Airbnb ROI: -1.41% Traditional ROI: 2.55%
6208 ARALIA IVY Lane Winter Garden, FL You found it! Amazing LOCATION and priced to sell! You will love the open floorplan and PR...	3 beds \| 3 baths \| 1,560 sq.ft.	$390,000	Airbnb cash on cash: -1.6% Traditional cash on cash: 2.86% Airbnb Rental Income: $1303 Traditional Rental Income: $2531 Airbnb ROI: -1.6% Traditional ROI: 2.86%
7276 WINDY WILLOW Street Winter Garden, FL Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-...	3 beds \| 3 baths \| 1,764 sq.ft.	$456,213	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.25% Airbnb Rental Income: $1303 Traditional Rental Income: $2108 Airbnb ROI: -0.59% Traditional ROI: 2.25%
7272 WINDY WILLOW Street Winter Garden, FL Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-...	3 beds \| 3 baths \| 1,697 sq.ft.	$483,258	Airbnb cash on cash: -0.66% Traditional cash on cash: 2% Airbnb Rental Income: $1303 Traditional Rental Income: $2099 Airbnb ROI: -0.66% Traditional ROI: 2%
13765 GOLDEN RUSSET Drive Winter Garden, FL Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2.5-bath townhome with a ...	3 beds \| 3 baths \| 1,600 sq.ft.	$365,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 3.03% Airbnb Rental Income: $1303 Traditional Rental Income: $2306 Airbnb ROI: -1.08% Traditional ROI: 3.03%
10607 WORDS Drive Winter Garden, FL Welcome to this beautifully maintained 4-bedroom, 2.5-bath home in the highly desirable St...	4 beds \| 3 baths \| 1,992 sq.ft.	$434,900	Airbnb cash on cash: 5.6% Traditional cash on cash: 4.06% Airbnb Rental Income: $4271 Traditional Rental Income: $2743 Airbnb ROI: 5.6% Traditional ROI: 4.06%
15014 WINDFLOWER Alley Winter Garden, FL Beautiful corner-unit townhome featuring 3 bedrooms and 2.5 bathrooms in the highly desira...	3 beds \| 3 baths \| 1,536 sq.ft.	$424,990	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.34% Airbnb Rental Income: $1303 Traditional Rental Income: $2374 Airbnb ROI: -0.37% Traditional ROI: 3.34%
16306 PRAIRIE SCHOOL Drive Winter Garden, FL Priced to sell! Great location and highly desired community! Located in the highly sought-...	3 beds \| 3 baths \| 1,792 sq.ft.	$415,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.01% Airbnb Rental Income: $1303 Traditional Rental Income: $2611 Airbnb ROI: -0.4% Traditional ROI: 4.01%
10648 WORDS Drive Winter Garden, FL Storey Grove *YES IT HAS A BACKYARD!!BACKS TO GREENSPACE!! 2023 built Open floorpla...	3 beds \| 3 baths \| 1,636 sq.ft.	$418,500	Airbnb cash on cash: -0.26% Traditional cash on cash: 3.88% Airbnb Rental Income: $1303 Traditional Rental Income: $2519 Airbnb ROI: -0.26% Traditional ROI: 3.88%
15056 WINDFLOWER Alley Winter Garden, FL ** PRICED TO SELL!! Excellent opportunity for homeowners or investors in the highly desira...	3 beds \| 3 baths \| 1,536 sq.ft.	$398,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.63% Airbnb Rental Income: $1303 Traditional Rental Income: $2374 Airbnb ROI: -0.33% Traditional ROI: 3.63%
300 ERON Way #1 Winter Garden, FL Welcome to low-maintenance living in the heart of Winter Garden! This charming 2-bedroom, ...	2 beds \| 2 baths \| 840 sq.ft.	$229,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 4.9% Airbnb Rental Income: $1522 Traditional Rental Income: $1651 Airbnb ROI: 2.26% Traditional ROI: 4.9%
15613 ORANGE HARVEST Loop Winter Garden, FL Virtually Staged. Welcome Home to 15163 Orange Harvest Drive! YOUR oportunity to live in t...	3 beds \| 3 baths \| 1,844 sq.ft.	$465,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.61% Airbnb Rental Income: $1303 Traditional Rental Income: $2628 Airbnb ROI: -0.37% Traditional ROI: 3.61%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Garden, FL

1424 SCARLET OAK Loop

Winter Garden, FL

3 beds | 3 baths | 1,737 sq.ft.

$379,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $1303

Traditional Rental Income: $2544

Airbnb ROI: -0.07%

Traditional ROI: 4.56%

760 WALKERS GROVE Lane

Winter Garden, FL

3 beds | 3 baths | 1,915 sq.ft.

$540,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $1303

Traditional Rental Income: $2695

Airbnb ROI: -0.58%

Traditional ROI: 2.99%

8873 FOUNTAIN PALM Alley

Winter Garden, FL

3 beds | 3 baths | 2,162 sq.ft.

$565,000

Airbnb cash on cash: -1.95%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $1303

Traditional Rental Income: $3264

Airbnb ROI: -1.95%

Traditional ROI: 2.54%

131 OAK LAUREL Drive

Winter Garden, FL

3 beds | 4 baths | 1,906 sq.ft.

$799,000

Airbnb cash on cash: -1.95%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $1303

Traditional Rental Income: $3797

Airbnb ROI: -1.95%

Traditional ROI: 1.95%

10509 SPRING ARBOR Lane

Winter Garden, FL

3 beds | 3 baths | 1,868 sq.ft.

$439,000

Airbnb cash on cash: -1.44%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $1303

Traditional Rental Income: $2686

Airbnb ROI: -1.44%

Traditional ROI: 2.91%

11025 SUSPENSE Drive

Winter Garden, FL

3 beds | 3 baths | 1,636 sq.ft.

$410,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1303

Traditional Rental Income: $2591

Airbnb ROI: -0.96%

Traditional ROI: 3.45%

5618 WATER ROSE Road

Winter Garden, FL

3 beds | 3 baths | 1,755 sq.ft.

$375,000

Airbnb cash on cash: -2.1%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $1303

Traditional Rental Income: $2749

Airbnb ROI: -2.1%

Traditional ROI: 3.16%

8878 BISMARCK PALM Drive

Winter Garden, FL

4 beds | 4 baths | 2,581 sq.ft.

$629,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $4271

Traditional Rental Income: $3376

Airbnb ROI: 2.06%