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.

Condos for Sale in Winter Garden, FL

Search for Condo for Sale in Winter Garden, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 114 Condo 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
27 Windtree Ln #102 Winter Garden, FL Welcome home to this bright, beautifully maintained and thoughtfully updated first-floor c...	2 beds \| 2 baths \| 918 sq.ft.	$224,995	Airbnb cash on cash: 3.02% Traditional cash on cash: 5.67% Airbnb Rental Income: $1522 Traditional Rental Income: $1656 Airbnb ROI: 3.02% Traditional ROI: 5.67%
373 Eron Way #47 Winter Garden, FL Short Sale. SHORT SALE APPROVED READY TO CLOSE AND MOVE-IN READY and quietly positioned wi...	2 beds \| 2 baths \| 840 sq.ft.	$182,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 5.54% Airbnb Rental Income: $1522 Traditional Rental Income: $1885 Airbnb ROI: 0.88% Traditional ROI: 5.54%
14501 Grove Resort Ave #1111 Winter Garden, FL Pond and Fountain Views \| Aggressively Priced \| Desirable Ground floor residence featuring...	2 beds \| 2 baths \| 1,265 sq.ft.	$179,000	Airbnb cash on cash: -4.45% Traditional cash on cash: 4.69% Airbnb Rental Income: $1522 Traditional Rental Income: $2636 Airbnb ROI: -4.45% Traditional ROI: 4.69%
14501 Grove Resort Ave #3303 Winter Garden, FL Experience the ultimate vacation lifestyle and investment opportunity at Grove Resort & Sp...	2 beds \| 2 baths \| 1,265 sq.ft.	$215,000	Airbnb cash on cash: -3.91% Traditional cash on cash: 1.7% Airbnb Rental Income: $1522 Traditional Rental Income: $2223 Airbnb ROI: -3.91% Traditional ROI: 1.7%
14501 Grove Resort Ave #3202 Winter Garden, FL Welcome to Your Perfect Orlando Investment & Vacation Escape! This beautifully appointed c...	3 beds \| 2 baths \| 1,396 sq.ft.	$350,000	Airbnb cash on cash: -3.4% Traditional cash on cash: 2.02% Airbnb Rental Income: $1303 Traditional Rental Income: $2677 Airbnb ROI: -3.4% Traditional ROI: 2.02%
14501 Grove Resort Ave #1409 Winter Garden, FL Property in excellent condition ready to go, very good source of extra revenue, do not let...	3 beds \| 2 baths \| 1,396 sq.ft.	$387,900	Airbnb cash on cash: -3.23% Traditional cash on cash: 0.48% Airbnb Rental Income: $1303 Traditional Rental Income: $2246 Airbnb ROI: -3.23% Traditional ROI: 0.48%
14501 Grove Resort Ave #3535 Winter Garden, FL New reduced Price: $369,990. GREAT NEW OWNER FINANCING AVAILABLE: CONTACT US FOR ADDITIONA...	2 beds \| 2 baths \| 1,434 sq.ft.	$369,990	Airbnb cash on cash: -3.31% Traditional cash on cash: 1.67% Airbnb Rental Income: $1522 Traditional Rental Income: $2808 Airbnb ROI: -3.31% Traditional ROI: 1.67%
14501 GROVE RESORT Avenue #1440 Winter Garden, FL Seller is offering $5,000 toward the buyer's closing costs, making this fully furnished co...	2 beds \| 2 baths \| 1,375 sq.ft.	$245,000	Airbnb cash on cash: -3.62% Traditional cash on cash: 3.26% Airbnb Rental Income: $1522 Traditional Rental Income: $2672 Airbnb ROI: -3.62% Traditional ROI: 3.26%
14501 Grove Resort Ave #1535 Winter Garden, FL GREAT NEW PRICE: $410,990.00. MOTIVATED SELLER. GREAT OWNER FINANCING AVAILABLE. BEAUTIFUL...	3 beds \| 2 baths \| 1,396 sq.ft.	$410,990	Airbnb cash on cash: -3.38% Traditional cash on cash: 1.15% Airbnb Rental Income: $1303 Traditional Rental Income: $2639 Airbnb ROI: -3.38% Traditional ROI: 1.15%
14501 Grove Resort Ave #3215 Winter Garden, FL Located on the second floor of Building 3, closest to the Safari Water Park, this fully fu...	2 beds \| 2 baths \| 1,265 sq.ft.	$199,000	Airbnb cash on cash: -4.12% Traditional cash on cash: 4.03% Airbnb Rental Income: $1522 Traditional Rental Income: $2617 Airbnb ROI: -4.12% Traditional ROI: 4.03%
14501 Grove Resort Ave #1443 Winter Garden, FL GREAT $10K PRICE REDUCTION: NEW PRICE $290,000.00 MOTIVATED SELLER. WELCOME TO THE GROVE R...	2 beds \| 2 baths \| 1,375 sq.ft.	$290,000	Airbnb cash on cash: -3.57% Traditional cash on cash: 2.46% Airbnb Rental Income: $1522 Traditional Rental Income: $2726 Airbnb ROI: -3.57% Traditional ROI: 2.46%
14501 Grove Resort Ave #1220 Winter Garden, FL The Birch - 2 Bed / 2 Bath Condo-Hotel The only floorplan at The Grove with two true prima...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -2.41% Traditional cash on cash: 3.18% Airbnb Rental Income: $1522 Traditional Rental Income: $2792 Airbnb ROI: -2.41% Traditional ROI: 3.18%
14501 Grove Resort Ave #2342 Winter Garden, FL Welcome to The Grove Resort & Water Park Orlando, a premier vacation resort just minutes f...	3 beds \| 3 baths \| 1,544 sq.ft.	$319,000	Airbnb cash on cash: -7.15% Traditional cash on cash: -1.18% Airbnb Rental Income: $1303 Traditional Rental Income: $2688 Airbnb ROI: -7.15% Traditional ROI: -1.18%
14501 Grove Resort Ave #3109 Winter Garden, FL PREMIUM BUILDING 3 \| RARE 14-FOOT CEILINGS \| ELEVATOR-FREE ACCESS \| ONSITE RENTAL PROGRAM ...	2 beds \| 2 baths \| 1,434 sq.ft.	$299,900	Airbnb cash on cash: -3.02% Traditional cash on cash: 3.31% Airbnb Rental Income: $1522 Traditional Rental Income: $2867 Airbnb ROI: -3.02% Traditional ROI: 3.31%
14501 Grove Resort Ave #1622 Winter Garden, FL BEST VIEW IN THE ENTIRE RESORT! This is the largest condo offered at The Grove Resort & Wa...	3 beds \| 3 baths \| 1,544 sq.ft.	$449,000	Airbnb cash on cash: -3.22% Traditional cash on cash: 1.81% Airbnb Rental Income: $1303 Traditional Rental Income: $3011 Airbnb ROI: -3.22% Traditional ROI: 1.81%
14200 Avalon Rd #406 Winter Garden, FL Discover your next investment or dream home! This spacious 3-bedroom, 2-bathroom condo off...	3 beds \| 2 baths \| 1,288 sq.ft.	$213,000	Airbnb cash on cash: -2.42% Traditional cash on cash: 4.48% Airbnb Rental Income: $1303 Traditional Rental Income: $2334 Airbnb ROI: -2.42% Traditional ROI: 4.48%
14501 Grove Resort Ave #2101 Winter Garden, FL Experience resort-style living and exceptional investment potential with this luxurious fi...	3 beds \| 3 baths \| 1,544 sq.ft.	$460,000	Airbnb cash on cash: -3.16% Traditional cash on cash: 1.42% Airbnb Rental Income: $1303 Traditional Rental Income: $2870 Airbnb ROI: -3.16% Traditional ROI: 1.42%
14501 GROVE RESORT Avenue #1407 Winter Garden, FL Waterpark View- NEW PRICE! Enjoy sweeping waterpark views from this spacious Sable floor p...	3 beds \| 3 baths \| 1,544 sq.ft.	$225,000	Airbnb cash on cash: -5.16% Traditional cash on cash: 3.68% Airbnb Rental Income: $1303 Traditional Rental Income: $2778 Airbnb ROI: -5.16% Traditional ROI: 3.68%
14501 Grove Resort Ave #1637 Winter Garden, FL NEW PRICE:$235,100.00 VERY MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CO...	2 beds \| 2 baths \| 1,375 sq.ft.	$235,100	Airbnb cash on cash: -4.31% Traditional cash on cash: 3.4% Airbnb Rental Income: $1522 Traditional Rental Income: $2792 Airbnb ROI: -4.31% Traditional ROI: 3.4%
14501 Grove Resort Ave #3231 Winter Garden, FL TOWER 3 LOCATION CLOSEST TO THE WATERPARK! Exceptional opportunity to own at The Grove Res...	2 beds \| 2 baths \| 1,375 sq.ft.	$190,000	Airbnb cash on cash: -3.82% Traditional cash on cash: 2.25% Airbnb Rental Income: $1522 Traditional Rental Income: $2175 Airbnb ROI: -3.82% Traditional ROI: 2.25%
14501 Grove Resort Ave #3128 Winter Garden, FL Location, location. location, Spacious 3-bedroom, 3-bathroom condo inside the highly desir...	3 beds \| 3 baths \| 1,544 sq.ft.	$250,000	Airbnb cash on cash: -4.48% Traditional cash on cash: 3.64% Airbnb Rental Income: $1303 Traditional Rental Income: $2816 Airbnb ROI: -4.48% Traditional ROI: 3.64%
14501 Grove Resort Ave #1105 Winter Garden, FL Skip the Elevator. Start the Vacation. First-floor units in Tower 1 at The Grove Resort do...	2 beds \| 2 baths \| 1,265 sq.ft.	$304,000	Airbnb cash on cash: -2.35% Traditional cash on cash: 3.26% Airbnb Rental Income: $1522 Traditional Rental Income: $2685 Airbnb ROI: -2.35% Traditional ROI: 3.26%
14501 Grove Resort Ave #2214 Winter Garden, FL Opportunity Knocks with an amazing Price!! Looking for an Investment Fully Furnished STR t...	2 beds \| 2 baths \| 1,375 sq.ft.	$235,000	Airbnb cash on cash: -4.81% Traditional cash on cash: -0.04% Airbnb Rental Income: $1522 Traditional Rental Income: $2139 Airbnb ROI: -4.81% Traditional ROI: -0.04%
68 Windtree Ln #201 Winter Garden, FL Come and see why this spacious 2 bedrooms, 2 bathrooms second floor open floor plan condo ...	2 beds \| 2 baths \| 918 sq.ft.	$214,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 5.75% Airbnb Rental Income: $1522 Traditional Rental Income: $1971 Airbnb ROI: 1.35% Traditional ROI: 5.75%
14501 Grove Resort Ave #1746 Winter Garden, FL Welcome to The Grove, a secluded condo-hotel set on the shores of Lake Austin. Turning int...	2 beds \| 2 baths \| 1,375 sq.ft.	$210,000	Airbnb cash on cash: -3.4% Traditional cash on cash: 5.62% Airbnb Rental Income: $1522 Traditional Rental Income: $2874 Airbnb ROI: -3.4% Traditional ROI: 5.62%
14501 Grove Resort Ave #3538 Winter Garden, FL Motivated Seller - Spacious 3-Bedroom Condo on the 5th Floor! Step into the popular Jasmin...	3 beds \| 2 baths \| 1,396 sq.ft.	$351,450	Airbnb cash on cash: -3.29% Traditional cash on cash: 2.16% Airbnb Rental Income: $1303 Traditional Rental Income: $2694 Airbnb ROI: -3.29% Traditional ROI: 2.16%
14501 Grove Resort Ave #1703 Winter Garden, FL RARE opportunity to own a TOP-FLOOR UNIT with SWEEPING LAKE VIEWS! This 3-bedroom, 2-bathr...	3 beds \| 2 baths \| 1,396 sq.ft.	$299,000	Airbnb cash on cash: -4.3% Traditional cash on cash: 0.51% Airbnb Rental Income: $1303 Traditional Rental Income: $2251 Airbnb ROI: -4.3% Traditional ROI: 0.51%
14501 Grove Resort Ave #2542 Winter Garden, FL The lowest-priced 3-bedroom/3-bath on a higher floor at The Grove Resort & Water Park! Thi...	3 beds \| 3 baths \| 1,544 sq.ft.	$205,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 7.1% Airbnb Rental Income: $1303 Traditional Rental Income: $2387 Airbnb ROI: -0.56% Traditional ROI: 7.1%
14501 Grove Resort Ave Winter Garden, FL Luxury vacation home ownership 5 minutes from Walt Disney World Park. Dazzling new resort ...	3 beds \| 3 baths \| 1,544 sq.ft.	$335,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.78% Airbnb Rental Income: $1522 Traditional Rental Income: $3155 Airbnb ROI: -1.14% Traditional ROI: 3.78%
417 Southern Pecan Cir #201 Winter Garden, FL NEWLY UPDATED LAMINATE FLOORING THROUGHOUT THE MAIN AREAS, BEDROOMS, AND STAIRS!!!! kITCHE...	2 beds \| 2 baths \| 1,264 sq.ft.	$275,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.07% Airbnb Rental Income: $1522 Traditional Rental Income: $2005 Airbnb ROI: -0.5% Traditional ROI: 3.07%
14501 Grove Resort Ave #2129 Winter Garden, FL HUGE PRICE REDUCTION! Don't miss this rare opportunity to own a fully furnished, turn-key ...	3 beds \| 2 baths \| 1,396 sq.ft.	$359,000	Airbnb cash on cash: -3.49% Traditional cash on cash: 2.52% Airbnb Rental Income: $1303 Traditional Rental Income: $2921 Airbnb ROI: -3.49% Traditional ROI: 2.52%
14501 Grove Resort Ave #3737 Winter Garden, FL Virtually Staged. Virtually Staged. Turn-Key, Fully Furnished 3-Bedroom Condo at The Grove...	3 beds \| 2 baths \| 1,396 sq.ft.	$350,000	Airbnb cash on cash: -3.45% Traditional cash on cash: 0.19% Airbnb Rental Income: $1303 Traditional Rental Income: $2092 Airbnb ROI: -3.45% Traditional ROI: 0.19%
14501 Grove Resort Ave #3714 Winter Garden, FL HUGE PRICE REDUCTION! Welcome to your fully furnished, turn-key 2-bedroom, 2-bath retreat ...	2 beds \| 2 baths \| 1,375 sq.ft.	$289,000	Airbnb cash on cash: -3.11% Traditional cash on cash: 4.4% Airbnb Rental Income: $1522 Traditional Rental Income: $3124 Airbnb ROI: -3.11% Traditional ROI: 4.4%
14501 Grove Resort Ave #2534 Winter Garden, FL THIS IS A MUST-SELL UNIT. Vacation investment opportunity at The Grove Resort & Water Park...	3 beds \| 2 baths \| 1,396 sq.ft.	$210,000	Airbnb cash on cash: -5.73% Traditional cash on cash: 3.61% Airbnb Rental Income: $1303 Traditional Rental Income: $2755 Airbnb ROI: -5.73% Traditional ROI: 3.61%
14501 Grove Resort Ave #2623 Winter Garden, FL 6th Floor Water View - Fully Furnished 2-Bedroom Condo at The Grove Resort Orlando Enjoy e...	2 beds \| 2 baths \| 1,265 sq.ft.	$390,000	Airbnb cash on cash: -2.3% Traditional cash on cash: 1.69% Airbnb Rental Income: $1522 Traditional Rental Income: $2536 Airbnb ROI: -2.3% Traditional ROI: 1.69%
14501 Grove Resort Ave #2334 Winter Garden, FL Escape to your own luxurious, fully furnished condo-hotel residence at the prestigious Gro...	3 beds \| 2 baths \| 1,396 sq.ft.	$274,900	Airbnb cash on cash: -3.86% Traditional cash on cash: 2.94% Airbnb Rental Income: $1303 Traditional Rental Income: $2659 Airbnb ROI: -3.86% Traditional ROI: 2.94%
14501 Grove Resort Ave #3222 Winter Garden, FL floorplans you can own, " The Palm" is located in Building 3 on the 2nd, Floor it has 2 Be...	2 beds \| 2 baths \| 1,265 sq.ft.	$330,000	Airbnb cash on cash: -3.02% Traditional cash on cash: 1.76% Airbnb Rental Income: $1522 Traditional Rental Income: $2564 Airbnb ROI: -3.02% Traditional ROI: 1.76%
330 Southern Pecan Cir #208 Winter Garden, FL Welcome to this amazing unit, nestled within the gated community of Southern Pines in the ...	3 beds \| 2 baths \| 1,453 sq.ft.	$298,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 4.1% Airbnb Rental Income: $1303 Traditional Rental Income: $2440 Airbnb ROI: -1.4% Traditional ROI: 4.1%
14501 Grove Resort Ave #3712 Winter Garden, FL Penthouse-level Jasmine floor plan at The Grove Resort and Waterpark. This spacious 3 bedr...	3 beds \| 2 baths \| 1,396 sq.ft.	$325,000	Airbnb cash on cash: -3.39% Traditional cash on cash: 2.56% Airbnb Rental Income: $1303 Traditional Rental Income: $2713 Airbnb ROI: -3.39% Traditional ROI: 2.56%
1300 EASTERN PECAN Place #208 Winter Garden, FL Beautiful 3-bedroom, 2-bath condominium located in the highly desirable gated community of...	3 beds \| 2 baths \| 1,453 sq.ft.	$287,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 4.23% Airbnb Rental Income: $1303 Traditional Rental Income: $2457 Airbnb ROI: -1.54% Traditional ROI: 4.23%

Your search for investment property begins and ends here

Condos for Sale in Winter Garden, FL

27 Windtree Ln #102

Winter Garden, FL

2 beds | 2 baths | 918 sq.ft.

$224,995

Airbnb cash on cash: 3.02%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $1522

Traditional Rental Income: $1656

Airbnb ROI: 3.02%

Traditional ROI: 5.67%

373 Eron Way #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$182,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1522

Traditional Rental Income: $1885

Airbnb ROI: 0.88%

Traditional ROI: 5.54%

14501 Grove Resort Ave #1111

Winter Garden, FL

2 beds | 2 baths | 1,265 sq.ft.

$179,000

Airbnb cash on cash: -4.45%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $1522

Traditional Rental Income: $2636

Airbnb ROI: -4.45%

Traditional ROI: 4.69%

14501 Grove Resort Ave #3303

Winter Garden, FL

2 beds | 2 baths | 1,265 sq.ft.

$215,000

Airbnb cash on cash: -3.91%

Traditional cash on cash: 1.7%

Airbnb Rental Income: $1522

Traditional Rental Income: $2223

Airbnb ROI: -3.91%

Traditional ROI: 1.7%

14501 Grove Resort Ave #3202

Winter Garden, FL

3 beds | 2 baths | 1,396 sq.ft.

$350,000

Airbnb cash on cash: -3.4%

Traditional cash on cash: 2.02%

Airbnb Rental Income: $1303

Traditional Rental Income: $2677

Airbnb ROI: -3.4%

Traditional ROI: 2.02%

14501 Grove Resort Ave #1409

Winter Garden, FL

3 beds | 2 baths | 1,396 sq.ft.

$387,900

Airbnb cash on cash: -3.23%

Traditional cash on cash: 0.48%

Airbnb Rental Income: $1303

Traditional Rental Income: $2246

Airbnb ROI: -3.23%

Traditional ROI: 0.48%

14501 Grove Resort Ave #3535

Winter Garden, FL

2 beds | 2 baths | 1,434 sq.ft.

$369,990

Airbnb cash on cash: -3.31%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $1522

Traditional Rental Income: $2808

Airbnb ROI: -3.31%

Traditional ROI: 1.67%

14501 GROVE RESORT Avenue #1440

Winter Garden, FL

2 beds | 2 baths | 1,375 sq.ft.

$245,000

Airbnb cash on cash: -3.62%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $1522

Traditional Rental Income: $2672

Airbnb ROI: -3.62%