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
7279 DUXBURY LANE Winter Garden, FL Welcome to this stunning END UNIT townhome in the highly desirable Lakeview Pointe communi...	3 beds \| 3 baths \| 1,895 sq.ft.	$438,100	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.84% Airbnb Rental Income: $1636 Traditional Rental Income: $2710 Airbnb ROI: -0.9% Traditional ROI: 2.84%
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%
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.	$465,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 4.32% Airbnb Rental Income: $1636 Traditional Rental Income: $3086 Airbnb ROI: -0.07% Traditional ROI: 4.32%
5755 CYPRESS HILL ROAD Winter Garden, FL Welcome to this beautifully maintained corner townhouse in the sought-after Orchard Hills ...	3 beds \| 3 baths \| 1,797 sq.ft.	$455,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.31% Airbnb Rental Income: $1636 Traditional Rental Income: $2722 Airbnb ROI: -0.33% Traditional ROI: 3.31%
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.	$460,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.72% Airbnb Rental Income: $1636 Traditional Rental Income: $2487 Airbnb ROI: -0.32% Traditional ROI: 2.72%
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%
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.	$834,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 1.83% Airbnb Rental Income: $1636 Traditional Rental Income: $3797 Airbnb ROI: -1.55% Traditional ROI: 1.83%
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.	$425,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 4.14% Airbnb Rental Income: $1636 Traditional Rental Income: $3164 Airbnb ROI: -0.85% Traditional ROI: 4.14%
1158 ORANGE SEASON LANE Winter Garden, FL Located in the gated community of Hickory Hammock, this beautiful corner-unit townhouse of...	3 beds \| 3 baths \| 2,444 sq.ft.	$525,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 2.73% Airbnb Rental Income: $1636 Traditional Rental Income: $2978 Airbnb ROI: -0.95% Traditional ROI: 2.73%
15508 BLACKBEAD STREET Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. If...	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%
11025 SUSPENSE DRIVE Winter Garden, FL Beautifully maintained and thoughtfully upgraded townhome in the Storey Grove community of...	3 beds \| 3 baths \| 1,636 sq.ft.	$435,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.2% Airbnb Rental Income: $1636 Traditional Rental Income: $2591 Airbnb ROI: -0.28% Traditional ROI: 3.2%
980 STUCKI TERRACE Winter Garden, FL Here is your opportunity to own this affordable corner unit townhome. Charming 3 bedroom, ...	3 beds \| 2 baths \| 984 sq.ft.	$230,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 4% Airbnb Rental Income: $1636 Traditional Rental Income: $1727 Airbnb ROI: 1.46% Traditional ROI: 4%
5618 WATER ROSE ROAD Winter Garden, FL This two-story townhome consists of three bedrooms, two and a half bathrooms, and a two-ca...	3 beds \| 3 baths \| 1,755 sq.ft.	$395,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 3.33% Airbnb Rental Income: $1636 Traditional Rental Income: $2749 Airbnb ROI: -0.92% Traditional ROI: 3.33%
11187 HANLON TERRACE ALLEY Winter Garden, FL Under contract-accepting backup offers. Welcome to this beautifully maintained two-story t...	4 beds \| 3 baths \| 2,200 sq.ft.	$399,900	Airbnb cash on cash: 6.84% Traditional cash on cash: 4.94% Airbnb Rental Income: $5064 Traditional Rental Income: $3320 Airbnb ROI: 6.84% Traditional ROI: 4.94%
14971 APOLLO BOND DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. This luxurious townhouse, built in 2019, i...	3 beds \| 3 baths \| 1,655 sq.ft.	$414,900	Airbnb cash on cash: -0.51% Traditional cash on cash: 4.04% Airbnb Rental Income: $1636 Traditional Rental Income: $2942 Airbnb ROI: -0.51% Traditional ROI: 4.04%
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: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $3923 Airbnb ROI: N/A Traditional ROI: 2.26%
16434 HAMLIN HILLS ROAD Winter Garden, FL Beautiful 3-bedroom, 2.5-bathroom townhouse located in the highly desirable Hamlin Hills a...	3 beds \| 3 baths \| 1,729 sq.ft.	$480,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 4.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2920 Airbnb ROI: 0.8% Traditional ROI: 4.68%
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: 0.72% Traditional cash on cash: 5.64% Airbnb Rental Income: $1636 Traditional Rental Income: $3152 Airbnb ROI: 0.72% Traditional ROI: 5.64%
15098 WINDFLOWER ALLEY Winter Garden, FL Welcome to Osprey Ranch, where modern design, LOW MAINTENANCE LIVING and an unbeatable Win...	2 beds \| 3 baths \| 1,276 sq.ft.	$355,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.62% Airbnb Rental Income: $2340 Traditional Rental Income: $2699 Airbnb ROI: 1.81% Traditional ROI: 4.62%
7363 MEZZANO LANE Winter Garden, FL Welcome to your chance to own one of the most desirable residences in this vibrant communi...	4 beds \| 4 baths \| 1,920 sq.ft.	$469,999	Airbnb cash on cash: 6.08% Traditional cash on cash: 4.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3220 Airbnb ROI: 6.08% Traditional ROI: 4.23%
1286 WINTER GREEN WAY Winter Garden, FL Motivated sellers!!! Sellers are offering $10,000 in concessions for the renovation of a n...	2 beds \| 2 baths \| 1,144 sq.ft.	$229,900	Airbnb cash on cash: 5.84% Traditional cash on cash: 7.33% Airbnb Rental Income: $2340 Traditional Rental Income: $2085 Airbnb ROI: 5.84% Traditional ROI: 7.33%
15663 KINNOW MANDARIN LANE Winter Garden, FL ANOTHER MASSIVE PRICE REDUCTION!! SELLERS ARE HIGHLY MOTIVATED!! This is your chance t...	3 beds \| 3 baths \| 1,868 sq.ft.	$399,900	Airbnb cash on cash: -0.92% Traditional cash on cash: 4.32% Airbnb Rental Income: $1636 Traditional Rental Income: $3140 Airbnb ROI: -0.92% Traditional ROI: 4.32%
15684 Orange Harvest Lp Winter Garden, FL Welcome to 15684 Orange Harvest Loop, a 3-bedroom, 2.5-bath townhouse with a loft, located...	3 beds \| 3 baths \| 2,012 sq.ft.	$459,900	Airbnb cash on cash: -0.59% Traditional cash on cash: 5.92% Airbnb Rental Income: $1636 Traditional Rental Income: $3977 Airbnb ROI: -0.59% Traditional ROI: 5.92%
17724 PORTER ROAD Winter Garden, FL One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Ima...	3 beds \| 3 baths \| 1,644 sq.ft.	$471,735	Airbnb cash on cash: 0% Traditional cash on cash: 3.38% Airbnb Rental Income: $1636 Traditional Rental Income: $2666 Airbnb ROI: 0% Traditional ROI: 3.38%
16425 PRAIRIE SCHOOL DRIVE Winter Garden, FL Welcome to 16425 Prairie School Dr, an exceptional 2021-built residence offering 3 bedroom...	3 beds \| 3 baths \| 1,662 sq.ft.	$435,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.6% Airbnb Rental Income: $1636 Traditional Rental Income: $2901 Airbnb ROI: -0.64% Traditional ROI: 3.6%
5706 CYPRESS HILL ROAD Winter Garden, FL Welcome to 5706 Cypress Hill Rd, a 3-bedroom, 2.5-bath townhome located in the Orchard Hil...	3 beds \| 3 baths \| 1,712 sq.ft.	$460,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 3.57% Airbnb Rental Income: $1636 Traditional Rental Income: $3000 Airbnb ROI: -0.67% Traditional ROI: 3.57%
8113 RED STOPPER LANE Winter Garden, FL Perfectly positioned in the heart of Horizon West, this impeccably maintained 3-bedroom, 2...	3 beds \| 3 baths \| 1,725 sq.ft.	$444,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 4.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2930 Airbnb ROI: -0.2% Traditional ROI: 4.02%
15182 SUNRISE GROVE COURT Winter Garden, FL Welcome to 15183 Sunrise Grove Court, a beautiful townhome located in the highly sought-af...	3 beds \| 3 baths \| 1,844 sq.ft.	$384,990	Airbnb cash on cash: 0.1% Traditional cash on cash: 5.15% Airbnb Rental Income: $1636 Traditional Rental Income: $2999 Airbnb ROI: 0.1% Traditional ROI: 5.15%
7007 TWILIGHT BAY DRIVE Winter Garden, FL Attention investors!! Welcome to this beautiful townhome like new and rented until April 2...	3 beds \| 3 baths \| 1,845 sq.ft.	$465,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 5.1% Airbnb Rental Income: $1636 Traditional Rental Income: $3109 Airbnb ROI: 0.65% Traditional ROI: 5.1%
8156 WOOD SAGE DRIVE Winter Garden, FL Winter Garden â Rare, immaculate end-unit townhome in highly sought-after Summerlake, fu...	3 beds \| 3 baths \| 1,853 sq.ft.	$449,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 4.64% Airbnb Rental Income: $1636 Traditional Rental Income: $3165 Airbnb ROI: -0.1% Traditional ROI: 4.64%
13750 DANIELS LANDING CIRCLE Winter Garden, FL Under contract-accepting backup offers. Don't Miss This Rare End Unit Opportunity in Sough...	2 beds \| 3 baths \| 1,293 sq.ft.	$310,500	Airbnb cash on cash: 2.5% Traditional cash on cash: 5.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2565 Airbnb ROI: 2.5% Traditional ROI: 5.26%
6530 PASTURELANDS PLACE Winter Garden, FL DOWN PAYMENT ASSISTANCE AVAILABLE Welcome to your New Home with Brand New Inverter AC unit...	3 beds \| 3 baths \| 2,067 sq.ft.	$479,999	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.95% Airbnb Rental Income: $1636 Traditional Rental Income: $3051 Airbnb ROI: -0.23% Traditional ROI: 3.95%
7078 TWILIGHT BAY DRIVE Winter Garden, FL Welcome to Your Horizon West Sanctuary: The Madison at Mezzano. Experience the perfect bl...	3 beds \| 3 baths \| 2,032 sq.ft.	$462,500	Airbnb cash on cash: -0.45% Traditional cash on cash: 4.35% Airbnb Rental Income: $1636 Traditional Rental Income: $3252 Airbnb ROI: -0.45% Traditional ROI: 4.35%
15659 JUNGLE ALLEY Winter Garden, FL Seller motivated. Beautifully maintained town home 3 bed and 3 bath in the desirable Hori...	3 beds \| 3 baths \| 1,732 sq.ft.	$435,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.14% Airbnb Rental Income: $1636 Traditional Rental Income: $2996 Airbnb ROI: -0.33% Traditional ROI: 4.14%
13291 PEACEFUL MELODY DRIVE Winter Garden, FL One or more photo(s) has been virtually staged. Under Construction. Sample Images Harbor T...	3 beds \| 3 baths \| 1,644 sq.ft.	$428,405	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.41% Airbnb Rental Income: $1636 Traditional Rental Income: $2457 Airbnb ROI: 0.21% Traditional ROI: 3.41%
6212 ARALIA IVY LANE Winter Garden, FL LOCATION! LOCATION! LOCATION! This spacious and beautiful two-story townhome offers the pe...	3 beds \| 3 baths \| 1,560 sq.ft.	$430,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 3.72% Airbnb Rental Income: $1636 Traditional Rental Income: $2939 Airbnb ROI: -0.66% Traditional ROI: 3.72%
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: 5.88% Traditional cash on cash: 4.05% Airbnb Rental Income: $5064 Traditional Rental Income: $3198 Airbnb ROI: 5.88% Traditional ROI: 4.05%
1325 FETTLER WAY Winter Garden, FL Under contract-accepting backup offers. RENOVATED 3 Bed/2 bath PRIMARY SUITE DOWNSTAIRS, P...	3 beds \| 2 baths \| 1,440 sq.ft.	$279,900	Airbnb cash on cash: 1.56% Traditional cash on cash: 5.19% Airbnb Rental Income: $1636 Traditional Rental Income: $2133 Airbnb ROI: 1.56% Traditional ROI: 5.19%
16413 PRAIRIE SCHOOL DRIVE Winter Garden, FL Under contract-accepting backup offers. Built in 2021 and located in the desirable Hawksmo...	3 beds \| 3 baths \| 1,626 sq.ft.	$434,900	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.44% Airbnb Rental Income: $1636 Traditional Rental Income: $2432 Airbnb ROI: -0.65% Traditional ROI: 2.44%
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.	$535,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 3.98% Airbnb Rental Income: $5064 Traditional Rental Income: $3684 Airbnb ROI: 4.67% Traditional ROI: 3.98%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Garden, FL

7279 DUXBURY LANE

Winter Garden, FL

3 beds | 3 baths | 1,895 sq.ft.

$438,100

Airbnb cash on cash: -0.9%

Traditional cash on cash: 2.84%

Airbnb Rental Income: $1636

Traditional Rental Income: $2710

Airbnb ROI: -0.9%

Traditional ROI: 2.84%

14447 PRUNNINGWOOD PLACE

Winter Garden, FL

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%

900 WALKERS GROVE LANE

Winter Garden, FL

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

$465,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $1636

Traditional Rental Income: $3086

Airbnb ROI: -0.07%

Traditional ROI: 4.32%

5755 CYPRESS HILL ROAD

Winter Garden, FL

3 beds | 3 baths | 1,797 sq.ft.

$455,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1636

Traditional Rental Income: $2722

Airbnb ROI: -0.33%

Traditional ROI: 3.31%

8170 BLUEJACK OAK DRIVE

Winter Garden, FL

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

$460,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1636

Traditional Rental Income: $2487

Airbnb ROI: -0.32%

Traditional ROI: 2.72%

648 ORANGE BELT LOOP

Winter Garden, FL

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%

131 OAK LAUREL DRIVE

Winter Garden, FL

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

$834,000

Airbnb cash on cash: -1.55%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $1636

Traditional Rental Income: $3797

Airbnb ROI: -1.55%

Traditional ROI: 1.83%

15334 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

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

$425,000

Airbnb cash on cash: -0.85%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $1636

Traditional Rental Income: $3164

Airbnb ROI: -0.85%