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 68 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.	$474,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.66% Airbnb Rental Income: $5064 Traditional Rental Income: $2907 Airbnb ROI: 6.2% Traditional ROI: 3.66%
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.	$415,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.72% Airbnb Rental Income: $1636 Traditional Rental Income: $2512 Airbnb ROI: -0.72% Traditional ROI: 2.72%
1166 WESTSIDE DRIVE Winter Garden, FL Charming 3 bedroom, 2 bath townhome with desirable Winter Garden address. Step through the...	3 beds \| 2 baths \| 846 sq.ft.	$229,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 5.21% Airbnb Rental Income: $1636 Traditional Rental Income: $1728 Airbnb ROI: 2.65% Traditional ROI: 5.21%
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.	$355,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.06% Airbnb Rental Income: $2340 Traditional Rental Income: $2020 Airbnb ROI: 2.29% Traditional ROI: 3.06%
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.	$1,044,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 1.07% Airbnb Rental Income: $1636 Traditional Rental Income: $3876 Airbnb ROI: -1.71% Traditional ROI: 1.07%
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.	$264,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 4.67% Airbnb Rental Income: $2340 Traditional Rental Income: $1795 Airbnb ROI: 4.54% Traditional ROI: 4.67%
15522 MURCOTT BLOSSOM BOULEVARD Winter Garden, FL LUXURY END-UNIT TOWNHOME IN HORIZON WEST! Move right in to this beautiful former model-ho...	3 beds \| 3 baths \| 2,207 sq.ft.	$485,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.5% Airbnb Rental Income: $1636 Traditional Rental Income: $3526 Airbnb ROI: -0.68% Traditional ROI: 4.5%
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.	$409,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $1636 Traditional Rental Income: $2447 Airbnb ROI: 0.33% Traditional ROI: 3.64%
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.	$400,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 4.45% Airbnb Rental Income: $5064 Traditional Rental Income: $2937 Airbnb ROI: 7.37% Traditional ROI: 4.45%
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.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 3.79% Airbnb Rental Income: $5064 Traditional Rental Income: $3218 Airbnb ROI: 5.72% Traditional ROI: 3.79%
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.	$439,999	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.11% Airbnb Rental Income: $1636 Traditional Rental Income: $2653 Airbnb ROI: -0.48% Traditional ROI: 3.11%
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.	$485,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.16% Airbnb Rental Income: $1636 Traditional Rental Income: $2857 Airbnb ROI: -0.55% Traditional ROI: 3.16%
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.	$425,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.64% Airbnb Rental Income: $1636 Traditional Rental Income: $2360 Airbnb ROI: -0.34% Traditional ROI: 2.64%
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%
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%
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%
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%
10684 WORDS DRIVE Winter Garden, FL This elegant two story townhome includes three bedrooms, two and one-half bathrooms and a ...	3 beds \| 3 baths \| 1,636 sq.ft.	$415,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 3.03% Airbnb Rental Income: $1636 Traditional Rental Income: $2451 Airbnb ROI: -0.25% Traditional ROI: 3.03%
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.	$374,900	Airbnb cash on cash: 2.62% Traditional cash on cash: 4.16% Airbnb Rental Income: $2340 Traditional Rental Income: $2305 Airbnb ROI: 2.62% Traditional ROI: 4.16%
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.	$210,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 5.09% Airbnb Rental Income: $2340 Traditional Rental Income: $1592 Airbnb ROI: 5.94% Traditional ROI: 5.09%
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.	$419,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.53% Airbnb Rental Income: $1636 Traditional Rental Income: $2629 Airbnb ROI: -0.17% Traditional ROI: 3.53%
14897 EVERGREEN OAK LOOP Winter Garden, FL Under contract-accepting backup offers. **This property qualifies for a closing cost credi...	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.	$459,990	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.8% Airbnb Rental Income: $1636 Traditional Rental Income: $2650 Airbnb ROI: 0.37% Traditional ROI: 3.8%
1010 STUCKI TERRACE Winter Garden, FL Westside TownhomesAND THIS ONE BACKS TO THE POOL NO REAR NEIGHBOR REDUCED 10K TODAY**...	3 beds \| 2 baths \| 984 sq.ft.	$219,900	Airbnb cash on cash: 2.83% Traditional cash on cash: 5.64% Airbnb Rental Income: $1636 Traditional Rental Income: $1760 Airbnb ROI: 2.83% Traditional ROI: 5.64%
8130 RED STOPPER LANE Winter Garden, FL One or more photo(s) has been virtually staged. HUGE PRICE REDUCTION!!! Stunning townhome ...	3 beds \| 3 baths \| 1,851 sq.ft.	$429,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 3.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2682 Airbnb ROI: -0.73% Traditional ROI: 3.02%
9416 BOLSHOI ALLEY Winter Garden, FL Under Construction. Discover this stunning new construction townhome at 9416 Bolshoi Alley...	3 beds \| 3 baths \| 1,693 sq.ft.	$429,990	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.74% Airbnb Rental Income: $1636 Traditional Rental Income: $2491 Airbnb ROI: 0.47% Traditional ROI: 3.74%
9428 BOLSHOI ALLEY Winter Garden, FL Under Construction. Discover this stunning new construction townhome at 9428 Bolshoi Alley...	3 beds \| 3 baths \| 1,835 sq.ft.	$456,990	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.85% Airbnb Rental Income: $1636 Traditional Rental Income: $2656 Airbnb ROI: 0.38% Traditional ROI: 3.85%
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.	$399,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.92% Airbnb Rental Income: $1636 Traditional Rental Income: $2420 Airbnb ROI: -0.41% Traditional ROI: 2.92%
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.	$395,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.66% Airbnb Rental Income: $1636 Traditional Rental Income: $2697 Airbnb ROI: 0.55% Traditional ROI: 4.66%
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.	$490,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 3.97% Airbnb Rental Income: $5064 Traditional Rental Income: $3194 Airbnb ROI: 5.79% Traditional ROI: 3.97%
7399 MEZZANO LANE Winter Garden, FL PRICED TO SELL!! Experience the perfect blend of elegance and comfort in this exceptional ...	4 beds \| 4 baths \| 1,920 sq.ft.	$510,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3189 Airbnb ROI: 5.41% Traditional ROI: 3.64%
7369 MEZZANO LN Winter Garden, FL An exceptional opportunity has arrivedâwelcome to this beautifully designed 4-bedroom, 4...	4 beds \| 4 baths \| 1,920 sq.ft.	$485,000	Airbnb cash on cash: 5.92% Traditional cash on cash: 4.08% Airbnb Rental Income: $5064 Traditional Rental Income: $3196 Airbnb ROI: 5.92% Traditional ROI: 4.08%
15464 BLACKBEAD STREET #15464 Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to your dream townhome right in th...	3 beds \| 3 baths \| 1,853 sq.ft.	$455,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 2.9% Airbnb Rental Income: $1636 Traditional Rental Income: $2727 Airbnb ROI: -0.74% Traditional ROI: 2.9%
1519 PRIORY CIRCLE Winter Garden, FL Charming 3 bedroom, 2.5 bathroom, 2 car garage, with loft! Located in Winter Gardenâs de...	3 beds \| 3 baths \| 1,916 sq.ft.	$379,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.77% Airbnb Rental Income: $1636 Traditional Rental Income: $2674 Airbnb ROI: -0.45% Traditional ROI: 3.77%
16485 PRAIRIE SCHOOL DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to this well-maintained move in ready 3 be...	3 beds \| 3 baths \| 1,626 sq.ft.	$398,500	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.24% Airbnb Rental Income: $1636 Traditional Rental Income: $2465 Airbnb ROI: -0.22% Traditional ROI: 3.24%
12023 HOLYSTONE STREET Winter Garden, FL PRICE IMPROVEMENT! Welcome to Waterleigh, one of the most sought after communities in Hori...	3 beds \| 3 baths \| 1,816 sq.ft.	$449,999	Airbnb cash on cash: -0.49% Traditional cash on cash: 3.07% Airbnb Rental Income: $1636 Traditional Rental Income: $2671 Airbnb ROI: -0.49% Traditional ROI: 3.07%
15451 BAY BRIDGE STREET Winter Garden, FL Under Construction. Discover this exceptional new construction home located at 15451 Bay B...	3 beds \| 3 baths \| 1,693 sq.ft.	$444,990	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.63% Airbnb Rental Income: $1636 Traditional Rental Income: $2510 Airbnb ROI: 0.42% Traditional ROI: 3.63%

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.

$474,000

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $5064

Traditional Rental Income: $2907

Airbnb ROI: 6.2%

Traditional ROI: 3.66%

14801 EVERGREEN OAK LOOP

Winter Garden, FL

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

$415,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1636

Traditional Rental Income: $2512

Airbnb ROI: -0.72%

Traditional ROI: 2.72%

1166 WESTSIDE DRIVE

Winter Garden, FL

3 beds | 2 baths | 846 sq.ft.

$229,000

Airbnb cash on cash: 2.65%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $1636

Traditional Rental Income: $1728

Airbnb ROI: 2.65%

Traditional ROI: 5.21%

14421 VASHONS WAY

Winter Garden, FL

2 beds | 3 baths | 1,088 sq.ft.

$355,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2340

Traditional Rental Income: $2020

Airbnb ROI: 2.29%

Traditional ROI: 3.06%

149 S PARK AVENUE

Winter Garden, FL

3 beds | 4 baths | 2,938 sq.ft.

$1,044,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $1636

Traditional Rental Income: $3876

Airbnb ROI: -1.71%

Traditional ROI: 1.07%

428 SAND LIME ROAD

Winter Garden, FL

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

2 beds | 2 baths | 1,190 sq.ft.

$264,000

Airbnb cash on cash: 4.54%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $2340

Traditional Rental Income: $1795

Airbnb ROI: 4.54%

Traditional ROI: 4.67%

15522 MURCOTT BLOSSOM BOULEVARD

Winter Garden, FL

3 beds | 3 baths | 2,207 sq.ft.

$485,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1636

Traditional Rental Income: $3526

Airbnb ROI: -0.68%