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 71 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
14433 PLEACH ST Winter Garden, FL Under contract-accepting backup offers. END-UNIT IN HIGHLY SOUGHT-AFTER INDEPENDENCE! This...	3 beds \| 3 baths \| 1,639 sq.ft.	$419,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 2.46% Airbnb Rental Income: $1636 Traditional Rental Income: $2300 Airbnb ROI: -0.4% Traditional ROI: 2.46%
14815 DRIFTWATER DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to 14815 Driftwater Driveâan upd...	4 beds \| 3 baths \| 1,997 sq.ft.	$450,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 2.57% Airbnb Rental Income: $5064 Traditional Rental Income: $2686 Airbnb ROI: 5.76% Traditional ROI: 2.57%
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.	$518,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.03% Airbnb Rental Income: $1636 Traditional Rental Income: $2723 Airbnb ROI: -0.17% Traditional ROI: 3.03%
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 Rare 4-bedroom, 2.5-bathroom townhome offering over 2,000 SQFT of living space in a highly...	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 Located in the heart of Winter Garden, this 3 bedroom 2 bath townhome features a screened ...	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 This luxury 4bd/3ba townhouse is located in the highly sought-after Hamlin Reserve at Wint...	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%
15206 SUNRISE GROVE COURT Winter Garden, FL Under contract-accepting backup offers. For the first time on the market, this impeccably ...	3 beds \| 3 baths \| 1,874 sq.ft.	$398,800	Airbnb cash on cash: 0.32% Traditional cash on cash: 4.49% Airbnb Rental Income: $1636 Traditional Rental Income: $2733 Airbnb ROI: 0.32% Traditional ROI: 4.49%
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.	$1,099,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 0.97% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.67% Traditional ROI: 0.97%
15508 BLACKBEAD STREET Winter Garden, FL New PRICE!!!! This charming home features a long driveway, providing ample parking and a w...	3 beds \| 3 baths \| 1,754 sq.ft.	$449,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.82% Airbnb Rental Income: $1636 Traditional Rental Income: $2515 Airbnb ROI: -0.37% Traditional ROI: 2.82%
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%
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.	$455,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 3.8% Airbnb Rental Income: $5064 Traditional Rental Income: $2937 Airbnb ROI: 6.37% Traditional ROI: 3.8%
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.	$475,000	Airbnb cash on cash: 5.37% Traditional cash on cash: 3.54% Airbnb Rental Income: $5064 Traditional Rental Income: $3218 Airbnb ROI: 5.37% Traditional ROI: 3.54%
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%
9690 EMERALD BERRY DRIVE Winter Garden, FL This Beautifully Townhome located in WATERMARK, Winter Garden FL.MOTIVATED SELLERS OFFERIN...	3 beds \| 3 baths \| 1,810 sq.ft.	$465,440	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.21% Airbnb Rental Income: $1636 Traditional Rental Income: $2731 Airbnb ROI: -0.37% Traditional ROI: 3.21%
13229 CALMING BREEZE WAY Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. . ...	3 beds \| 3 baths \| 1,715 sq.ft.	$435,990	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.88% Airbnb Rental Income: $1636 Traditional Rental Income: $2691 Airbnb ROI: 0.17% Traditional ROI: 3.88%
16333 INGRAM HILLS ALY Winter Garden, FL Investors, vacation home buyers, and first-time buyers, discover your ideal HORIZON WEST h...	3 beds \| 3 baths \| 1,644 sq.ft.	$468,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 4.07% Airbnb Rental Income: $1636 Traditional Rental Income: $2653 Airbnb ROI: 0.7% Traditional ROI: 4.07%
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.	$449,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.45% Airbnb Rental Income: $1636 Traditional Rental Income: $2360 Airbnb ROI: -0.37% Traditional ROI: 2.45%
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%
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%
13114 SERENE GLADE ROAD Winter Garden, FL One or more photo(s) has been virtually staged. \ Images shown are for illustrative purpos...	3 beds \| 3 baths \| 1,715 sq.ft.	$429,990	Airbnb cash on cash: 0.19% Traditional cash on cash: -0.77% Airbnb Rental Income: $1636 Traditional Rental Income: $788 Airbnb ROI: 0.19% Traditional ROI: -0.77%
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.	$445,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.56% Airbnb Rental Income: $1636 Traditional Rental Income: $2760 Airbnb ROI: -0.24% Traditional ROI: 3.56%
10316 SPRING ARBOR LANE Winter Garden, FL Under contract-accepting backup offers. At $198/ sq ft, this unit is priced lower per sq f...	4 beds \| 3 baths \| 2,200 sq.ft.	$435,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.56% Airbnb Rental Income: $5064 Traditional Rental Income: $2818 Airbnb ROI: 6.54% Traditional ROI: 3.56%
13532 AUTUMN HARVEST AVENUE Winter Garden, FL Luxurious New Townhome by RockWell Homes. Discover the perfect blend of luxury and conven...	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%
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%
6524 CALAMONDIN DRIVE Winter Garden, FL Seller Motivated offering closing concessions! This is a true Gem in the heart of Haml...	4 beds \| 3 baths \| 1,853 sq.ft.	$428,500	Airbnb cash on cash: 6.62% Traditional cash on cash: 3.08% Airbnb Rental Income: $5064 Traditional Rental Income: $2608 Airbnb ROI: 6.62% Traditional ROI: 3.08%
15098 WINDFLOWER ALLEY Winter Garden, FL Charming townhouse in the heart of Winter Garden â Donât miss it! (One of the best pri...	2 beds \| 3 baths \| 1,284 sq.ft.	$364,990	Airbnb cash on cash: 2.71% Traditional cash on cash: 4.3% Airbnb Rental Income: $2340 Traditional Rental Income: $2305 Airbnb ROI: 2.71% Traditional ROI: 4.3%
16261 ADMIRALS COVE LANE Winter Garden, FL PRICE REDUCED & Seller is offering $5K towards closing costs or rate buy down. Seller wil...	3 beds \| 3 baths \| 1,814 sq.ft.	$448,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.39% Airbnb Rental Income: $1636 Traditional Rental Income: $2636 Airbnb ROI: -0.1% Traditional ROI: 3.39%
15201 SUMMER HARVEST STREET Winter Garden, FL Under Construction. Luxury New Townhome by RockWell Homes lot #21. Welcome to this stunnin...	4 beds \| 3 baths \| 2,163 sq.ft.	$556,530	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.25% Airbnb Rental Income: $5064 Traditional Rental Income: $2833 Airbnb ROI: 5.56% Traditional ROI: 3.25%
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.	$384,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 3.97% Airbnb Rental Income: $1636 Traditional Rental Income: $2408 Airbnb ROI: 0.55% Traditional ROI: 3.97%
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%
12190 PLUMPTON DRIVE Winter Garden, FL Beautiful 3-Bedroom Townhome in Winter Garden, FL â Move-In Ready! Welcome to your fu...	3 beds \| 3 baths \| 1,688 sq.ft.	$439,500	Airbnb cash on cash: 0.62% Traditional cash on cash: 3.48% Airbnb Rental Income: $1636 Traditional Rental Income: $2352 Airbnb ROI: 0.62% Traditional ROI: 3.48%
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%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Garden, FL

14433 PLEACH ST

Winter Garden, FL

3 beds | 3 baths | 1,639 sq.ft.

$419,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $1636

Traditional Rental Income: $2300

Airbnb ROI: -0.4%

Traditional ROI: 2.46%

14815 DRIFTWATER DRIVE

Winter Garden, FL

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

$450,000

Airbnb cash on cash: 5.76%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $5064

Traditional Rental Income: $2686

Airbnb ROI: 5.76%

Traditional ROI: 2.57%

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.

$518,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $1636

Traditional Rental Income: $2723

Airbnb ROI: -0.17%

Traditional ROI: 3.03%

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%