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
15140 SUNRISE GROVE COURT Winter Garden, FL Under contract-accepting backup offers. Imagine a life where lakeside serenity meets moder...	3 beds \| 3 baths \| 2,012 sq.ft.	$390,987	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.07% Airbnb Rental Income: $1636 Traditional Rental Income: $3302 Airbnb ROI: -0.74% Traditional ROI: 5.07%
14801 EVERGREEN OAK LOOP Winter Garden, FL Welcome to Your Dream Townhome! Perfectly situated on a desirable corner lot, this charmi...	3 beds \| 3 baths \| 1,741 sq.ft.	$399,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2814 Airbnb ROI: -0.71% Traditional ROI: 3.68%
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.	$485,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 4.1% Airbnb Rental Income: $1636 Traditional Rental Income: $3086 Airbnb ROI: -0.11% Traditional ROI: 4.1%
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 \| 1,713 sq.ft.	$465,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2487 Airbnb ROI: -0.33% Traditional ROI: 2.68%
8122 RED STOPPER LANE Winter Garden, FL Beautifully presented 3-bedroom, 2.5-bath townhome built in 2017, offering 1,784 SF of liv...	3 beds \| 3 baths \| 1,784 sq.ft.	$435,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.47% Airbnb Rental Income: $1636 Traditional Rental Income: $2783 Airbnb ROI: -0.48% Traditional ROI: 3.47%
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.	$869,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 1.71% Airbnb Rental Income: $1636 Traditional Rental Income: $3797 Airbnb ROI: -1.53% Traditional ROI: 1.71%
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.	$450,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 3.86% Airbnb Rental Income: $1636 Traditional Rental Income: $3164 Airbnb ROI: -0.86% Traditional ROI: 3.86%
15508 BLACKBEAD STREET Winter Garden, FL One or more photo(s) has been virtually staged. If youâre looking for low-maintenance li...	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%
428 SAND LIME ROAD Winter Garden, FL Short Sale. SHORT SALE APPROVED 3 bedroom, 1.5 bath townhome in Winter Garden Just a 7 mi...	3 beds \| 2 baths \| 1,234 sq.ft.	$220,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 8.96% Airbnb Rental Income: $1636 Traditional Rental Income: $2443 Airbnb ROI: 2.87% Traditional ROI: 8.96%
5637 WATER ROSE ROAD Winter Garden, FL *WINDERMERE HIGH SCHOOL* Price improvement â great opportunity in Signature Lakes / ...	3 beds \| 3 baths \| 1,617 sq.ft.	$419,990	Airbnb cash on cash: -0.72% Traditional cash on cash: 3.73% Airbnb Rental Income: $1636 Traditional Rental Income: $2923 Airbnb ROI: -0.72% Traditional ROI: 3.73%
15688 ORANGE HARVEST LOOP Winter Garden, FL Welcome to your own piece of paradise in the prestigious dual-gated enclave of Hickory Ham...	3 beds \| 3 baths \| 2,012 sq.ft.	$479,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 4.18% Airbnb Rental Income: $1636 Traditional Rental Income: $3293 Airbnb ROI: -0.54% Traditional ROI: 4.18%
11187 HANLON TERRACE ALLEY Winter Garden, FL Welcome to this beautifully maintained two-story townhouse in the heart of Winter Garden, ...	4 beds \| 3 baths \| 2,200 sq.ft.	$429,900	Airbnb cash on cash: 6.3% Traditional cash on cash: 4.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3320 Airbnb ROI: 6.3% Traditional ROI: 4.53%
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: -0.31% Traditional cash on cash: 4.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2942 Airbnb ROI: -0.31% Traditional ROI: 4.24%
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: 4.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3297 Airbnb ROI: 6.33% Traditional ROI: 4.5%
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%
12043 HOLYSTONE STREET Winter Garden, FL Under contract-accepting backup offers. Motivated Seller MOVE IN READY . Welcome to Wa...	3 beds \| 3 baths \| 1,568 sq.ft.	$385,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 4.44% Airbnb Rental Income: $1636 Traditional Rental Income: $2921 Airbnb ROI: -0.39% Traditional ROI: 4.44%
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: 4.71% Airbnb Rental Income: $1636 Traditional Rental Income: $3152 Airbnb ROI: -0.21% Traditional ROI: 4.71%
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.	$365,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.47% Airbnb Rental Income: $2340 Traditional Rental Income: $2699 Airbnb ROI: 1.73% Traditional ROI: 4.47%
13158 BOUNTY AVENUE Winter Garden, FL Welcome home to The Ibis Model at Waterleigh! This beautiful, spacious town home with 3 be...	3 beds \| 3 baths \| 1,567 sq.ft.	$395,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.07% Airbnb Rental Income: $1636 Traditional Rental Income: $2833 Airbnb ROI: -0.4% Traditional ROI: 4.07%
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.	$479,999	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.13% Airbnb Rental Income: $5064 Traditional Rental Income: $3220 Airbnb ROI: 5.93% Traditional ROI: 4.13%
6388 TABEBUIA PARKWAY Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 1,770 sq.ft.	$455,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 4.69% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 7.33% Traditional ROI: 4.69%
11079 HANLON TERRACE ALLEY Winter Garden, FL GREAT OPPORTUNITY! BEST priced home in the area! Welcome to 11079 Hanlon Terrace Aly, l...	3 beds \| 3 baths \| 1,868 sq.ft.	$393,990	Airbnb cash on cash: -0.66% Traditional cash on cash: 4.67% Airbnb Rental Income: $1636 Traditional Rental Income: $3144 Airbnb ROI: -0.66% Traditional ROI: 4.67%
1286 WINTER GREEN WAY Winter Garden, FL Discover this charming 2-bedroom, 1.5-bath townhouse located just 2 milesâabout 5 minute...	2 beds \| 2 baths \| 1,144 sq.ft.	$239,900	Airbnb cash on cash: 5.56% Traditional cash on cash: 6.99% Airbnb Rental Income: $2340 Traditional Rental Income: $2085 Airbnb ROI: 5.56% Traditional ROI: 6.99%
13282 SERENE GLADE ROAD Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. St...	3 beds \| 3 baths \| 1,644 sq.ft.	$456,497	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.75% Airbnb Rental Income: $1636 Traditional Rental Income: $2848 Airbnb ROI: 0.83% Traditional ROI: 4.75%
15663 KINNOW MANDARIN LANE Winter Garden, FL MASSIVE PRICE REDUCTION !! THIS PROPERTY IS LISTED OVER $10,000 BELOW CURRENT MARKET VALUE...	3 beds \| 3 baths \| 1,868 sq.ft.	$405,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 4.47% Airbnb Rental Income: $1636 Traditional Rental Income: $3140 Airbnb ROI: -0.71% Traditional ROI: 4.47%
13274 SERENE GLADE ROAD Winter Garden, FL One or more photo(s) has been virtually staged. Under Construction. Sample Images Porter T...	3 beds \| 3 baths \| 1,715 sq.ft.	$434,990	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.29% Airbnb Rental Income: $1636 Traditional Rental Income: $2847 Airbnb ROI: 0.18% Traditional ROI: 4.29%
8024 BLUEJACK OAK DRIVE Winter Garden, FL Welcome to this cozy and modern 3-bedroom, 2.5-bath townhouse located in the highly sought...	3 beds \| 3 baths \| 1,784 sq.ft.	$490,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.41% Airbnb Rental Income: $1636 Traditional Rental Income: $2889 Airbnb ROI: -0.33% Traditional ROI: 3.41%
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.	$469,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 5.78% Airbnb Rental Income: $1636 Traditional Rental Income: $3977 Airbnb ROI: -0.6% Traditional ROI: 5.78%
1009 STUCKI TERRACE Winter Garden, FL Under contract-accepting backup offers. A rare find! Fully renovated 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 984 sq.ft.	$249,900	Airbnb cash on cash: 2.38% Traditional cash on cash: 6.84% Airbnb Rental Income: $1636 Traditional Rental Income: $2226 Airbnb ROI: 2.38% Traditional ROI: 6.84%
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%
6982 TWILIGHT BAY DRIVE Winter Garden, FL Beautiful and well maintained two story townhouse in Winter Garden just 15 minutes from Ma...	4 beds \| 3 baths \| 1,860 sq.ft.	$475,000	Airbnb cash on cash: 6.03% Traditional cash on cash: 3.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3110 Airbnb ROI: 6.03% Traditional ROI: 3.96%
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%
13343 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.	$431,990	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.37% Airbnb Rental Income: $1636 Traditional Rental Income: $2460 Airbnb ROI: 0.2% Traditional ROI: 3.37%
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.	$454,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.91% Airbnb Rental Income: $1636 Traditional Rental Income: $2930 Airbnb ROI: -0.22% Traditional ROI: 3.91%
13930 DANIELS LANDING CIRCLE Winter Garden, FL Rare end unit townhome in move-in ready condition located behind the gated entrance of Dan...	2 beds \| 3 baths \| 1,240 sq.ft.	$299,500	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.36% Airbnb Rental Income: $2340 Traditional Rental Income: $2040 Airbnb ROI: 2.37% Traditional ROI: 3.36%
7333 DUXBURY LANE Winter Garden, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 3 baths \| 1,813 sq.ft.	$410,000	Airbnb cash on cash: -1% Traditional cash on cash: 2.83% Airbnb Rental Income: $1636 Traditional Rental Income: $2648 Airbnb ROI: -1% Traditional ROI: 2.83%
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.	$399,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.94% Airbnb Rental Income: $1636 Traditional Rental Income: $2999 Airbnb ROI: 0.06% Traditional ROI: 4.94%

Your search for investment property begins and ends here

Townhouses for Sale in Winter Garden, FL

15140 SUNRISE GROVE COURT

Winter Garden, FL

3 beds | 3 baths | 2,012 sq.ft.

$390,987

Airbnb cash on cash: -0.74%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1636

Traditional Rental Income: $3302

Airbnb ROI: -0.74%

Traditional ROI: 5.07%

14801 EVERGREEN OAK LOOP

Winter Garden, FL

3 beds | 3 baths | 1,741 sq.ft.

$399,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1636

Traditional Rental Income: $2814

Airbnb ROI: -0.71%

Traditional ROI: 3.68%

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.

$485,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $1636

Traditional Rental Income: $3086

Airbnb ROI: -0.11%

Traditional ROI: 4.1%

8170 BLUEJACK OAK DRIVE

Winter Garden, FL

3 beds | 3 baths | 1,713 sq.ft.

$465,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $1636

Traditional Rental Income: $2487

Airbnb ROI: -0.33%

Traditional ROI: 2.68%

8122 RED STOPPER LANE

Winter Garden, FL

3 beds | 3 baths | 1,784 sq.ft.

$435,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1636

Traditional Rental Income: $2783

Airbnb ROI: -0.48%

Traditional ROI: 3.47%

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.

$869,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $1636

Traditional Rental Income: $3797

Airbnb ROI: -1.53%