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.

Single Family Homes for Sale in Winter Garden, FL

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

Showing 454 Single Family Residential 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
849 SHADOWMOSS DRIVE Winter Garden, FL Prime Winter Garden Location \| Westfield Lakes Welcome to this lovely 5-bedroom, 3-bath...	5 beds \| 3 baths \| 2,620 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $3077 Airbnb ROI: N/A Traditional ROI: 2.87%
2200 ROMANUM DRIVE Winter Garden, FL Come see 2200 Romanum Dr, recently updated with fresh interior paint and partial flooring ...	4 beds \| 4 baths \| 2,561 sq.ft.	$550,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 3.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3451 Airbnb ROI: 4.61% Traditional ROI: 3.48%
14411 HAMPSHIRE BAY CIRCLE Winter Garden, FL Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers...	4 beds \| 5 baths \| 4,010 sq.ft.	$895,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 5.69% Airbnb Rental Income: $5064 Traditional Rental Income: $6971 Airbnb ROI: 2.16% Traditional ROI: 5.69%
338 WINDFORD COURT Winter Garden, FL Discover this move-in ready 3-bedroom, 2-bathroom CBS construction home in Winter Garden, ...	3 beds \| 2 baths \| 1,050 sq.ft.	$330,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 4.15% Airbnb Rental Income: $1636 Traditional Rental Income: $1930 Airbnb ROI: 1.71% Traditional ROI: 4.15%
14372 SUNBRIDGE CIRCLE Winter Garden, FL This is a unique opportunity to live in the highly sought-after gated community of Bradfor...	4 beds \| 5 baths \| 3,468 sq.ft.	$745,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 6.44% Airbnb Rental Income: $5064 Traditional Rental Income: $5980 Airbnb ROI: 3.64% Traditional ROI: 6.44%
2202 ROMANUM DRIVE Winter Garden, FL Welcome to your next home in the heart of Winter Gardenâwhere location, lifestyle, and u...	3 beds \| 2 baths \| 1,889 sq.ft.	$565,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.32% Airbnb Rental Income: $1636 Traditional Rental Income: $2435 Airbnb ROI: -0.07% Traditional ROI: 2.32%
14645 TULLAMORE LOOP Winter Garden, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the gated com...	3 beds \| 2 baths \| 1,703 sq.ft.	$455,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 3.13% Airbnb Rental Income: $1636 Traditional Rental Income: $2276 Airbnb ROI: 0.55% Traditional ROI: 3.13%
897 LANDRUM DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to one of Winter Garden's most coveted add...	4 beds \| 4 baths \| 3,012 sq.ft.	$899,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 1.96% Airbnb Rental Income: $5064 Traditional Rental Income: $3383 Airbnb ROI: 2.73% Traditional ROI: 1.96%
13536 SUNSET LAKES CIRCLE Winter Garden, FL Under contract-accepting backup offers. Experience luxury living in this gorgeous home in ...	5 beds \| 4 baths \| 3,389 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $6227 Airbnb ROI: N/A Traditional ROI: 3.93%
13377 Lake Butler Blvd Winter Garden, FL One or more photo(s) has been virtually staged. BACK ON MARKET: Buyer's inability to obtai...	5 beds \| 4 baths \| 6,000 sq.ft.	$5,995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $7090 Airbnb ROI: N/A Traditional ROI: 0.02%
14776 MAGNOLIA RIDGE LOOP Winter Garden, FL Discover Your Dream Home in the Exclusive Orchard Hills Community! This stunning reside...	4 beds \| 4 baths \| 2,876 sq.ft.	$880,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.79% Airbnb Rental Income: $5064 Traditional Rental Income: $3622 Airbnb ROI: 2.28% Traditional ROI: 1.79%
7558 BISHOP SQUARE DRIVE Winter Garden, FL Virtually Staged. Move-in-ready 4-bedroom-plus-office home with a rare, unobstructed fount...	4 beds \| 2 baths \| 1,952 sq.ft.	$554,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 2.93% Airbnb Rental Income: $5064 Traditional Rental Income: $3076 Airbnb ROI: 4.77% Traditional ROI: 2.93%
7266 DESERT MANDARIN STREET Winter Garden, FL Great investment opportunity! Welcome to this beautifully maintained home built in 2018, f...	4 beds \| 3 baths \| 2,365 sq.ft.	$595,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $5064 Traditional Rental Income: $2890 Airbnb ROI: 4.34% Traditional ROI: 2.29%
15518 FOUNTAIN COVE COURT Winter Garden, FL Nestled within the exclusive Marina Bay enclave of Waterleigh, one of Horizon Westâs mos...	3 beds \| 3 baths \| 2,040 sq.ft.	$574,990	Airbnb cash on cash: -1.15% Traditional cash on cash: 2.08% Airbnb Rental Income: $1636 Traditional Rental Income: $2911 Airbnb ROI: -1.15% Traditional ROI: 2.08%
5460 BOWMAN DRIVE Winter Garden, FL Under contract-accepting backup offers. Video Tour Available Welcome to Overlook at Ha...	3 beds \| 4 baths \| 2,474 sq.ft.	$585,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 2.11% Airbnb Rental Income: $1636 Traditional Rental Income: $2981 Airbnb ROI: -1.2% Traditional ROI: 2.11%
14501 GROVE RESORT AVENUE #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: -2.56% Traditional cash on cash: 2.02% Airbnb Rental Income: $1636 Traditional Rental Income: $2677 Airbnb ROI: -2.56% Traditional ROI: 2.02%
420 E CYPRESS STREET Winter Garden, FL Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on ...	3 beds \| 2 baths \| 1,616 sq.ft.	$420,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.29% Airbnb Rental Income: $1636 Traditional Rental Income: $2686 Airbnb ROI: 0.45% Traditional ROI: 4.29%
14755 MASTHEAD LANDING CIRCLE Winter Garden, FL Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-...	4 beds \| 2 baths \| 2,258 sq.ft.	$575,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 1.49% Airbnb Rental Income: $5064 Traditional Rental Income: $2492 Airbnb ROI: 4.36% Traditional ROI: 1.49%
8721 BAYVIEW CROSSING DRIVE Winter Garden, FL Amazing opportunity for a corner lot pool home, within the highly demanded Waterleigh - Ma...	4 beds \| 4 baths \| 2,842 sq.ft.	$679,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 3.56% Airbnb Rental Income: $5064 Traditional Rental Income: $4111 Airbnb ROI: 3.44% Traditional ROI: 3.56%
15852 SHOREBIRD LANE Winter Garden, FL Under contract-accepting backup offers. Stunning 2-Story Home in Winter Garden â 4 Bedro...	4 beds \| 5 baths \| 2,766 sq.ft.	$799,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 2.67% Airbnb Rental Income: $5064 Traditional Rental Income: $4262 Airbnb ROI: 2.36% Traditional ROI: 2.67%
7725 PURPLE FINCH STREET Winter Garden, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	3 beds \| 3 baths \| 2,195 sq.ft.	$530,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.83% Airbnb Rental Income: $1636 Traditional Rental Income: $2886 Airbnb ROI: -0.63% Traditional ROI: 2.83%
1701 E BAY STREET Winter Garden, FL Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden...	2 beds \| 2 baths \| 825 sq.ft.	$295,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.87% Airbnb Rental Income: $2340 Traditional Rental Income: $1685 Airbnb ROI: 4.15% Traditional ROI: 3.87%
1112 JUNIPER HAMMOCK COURT Winter Garden, FL Virtually Staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in...	4 beds \| 2 baths \| 2,545 sq.ft.	$515,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.01% Airbnb Rental Income: $5064 Traditional Rental Income: $3154 Airbnb ROI: 5.83% Traditional ROI: 4.01%
13542 SUNSET LAKES CIRCLE Winter Garden, FL A New Standard of Luxury...Welcome to 13542 Sunset Lakes Circle, the 5,450 square foot cro...	5 beds \| 6 baths \| 5,450 sq.ft.	$3,799,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.24% Airbnb Rental Income: $null Traditional Rental Income: $10412 Airbnb ROI: N/A Traditional ROI: 1.24%
634 FOSTER AVENUE Winter Garden, FL Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down ...	2 beds \| 1 baths \| 696 sq.ft.	$285,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 4.48% Airbnb Rental Income: $2340 Traditional Rental Income: $1916 Airbnb ROI: 3.9% Traditional ROI: 4.48%
1061 PORTMOOR WAY Winter Garden, FL Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the hig...	4 beds \| 2 baths \| 1,804 sq.ft.	$535,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 1.76% Airbnb Rental Income: $5064 Traditional Rental Income: $2376 Airbnb ROI: 5.07% Traditional ROI: 1.76%
14501 GROVE RESORT AVENUE #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: -1.35% Traditional cash on cash: 1.66% Airbnb Rental Income: $2340 Traditional Rental Income: $2808 Airbnb ROI: -1.35% Traditional ROI: 1.66%
20 E DIVISION STREET Winter Garden, FL Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a fl...	4 beds \| 3 baths \| 2,729 sq.ft.	$1,149,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 1.34% Airbnb Rental Income: $5064 Traditional Rental Income: $3262 Airbnb ROI: 2.06% Traditional ROI: 1.34%
14501 GROVE RESORT AVENUE #1440 Winter Garden, FL Seller is offering $5,000 toward the buyerâs closing costs, making this fully furnished ...	2 beds \| 2 baths \| 1,375 sq.ft.	$245,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.26% Airbnb Rental Income: $2340 Traditional Rental Income: $2672 Airbnb ROI: -0.68% Traditional ROI: 3.26%
14501 GROVE RESORT AVENUE #2602 Winter Garden, FL Experience the best of both worlds with this incredible fully furnished 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,396 sq.ft.	$299,000	Airbnb cash on cash: -3.47% Traditional cash on cash: 1.87% Airbnb Rental Income: $1636 Traditional Rental Income: $2678 Airbnb ROI: -3.47% Traditional ROI: 1.87%
14501 GROVE RESORT AVENUE #2119 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	3 beds \| 2 baths \| 1,396 sq.ft.	$224,000	Airbnb cash on cash: -4.15% Traditional cash on cash: 2.9% Airbnb Rental Income: $1636 Traditional Rental Income: $2671 Airbnb ROI: -4.15% Traditional ROI: 2.9%
14501 GROVE RESORT AVENUE #3215 Winter Garden, FL Welcome to Grove Resort! Located on the second floor of Building 3, this unit is your laun...	2 beds \| 2 baths \| 1,265 sq.ft.	$239,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.2% Airbnb Rental Income: $2340 Traditional Rental Income: $2617 Airbnb ROI: -0.59% Traditional ROI: 3.2%
6323 HAMLIN RESERVE BOULEVARD Winter Garden, FL Expansive private backyard. Covered brick paver patio. Carpet free interior. Wood look til...	3 beds \| 3 baths \| 2,177 sq.ft.	$560,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 2.08% Airbnb Rental Income: $1636 Traditional Rental Income: $2966 Airbnb ROI: -1.35% Traditional ROI: 2.08%
708 ORANGE BELT LOOP Winter Garden, FL LOCATED IN THE HIGHLY SOUGHT AFTER GOLF CART DISTRICT OF DOWNTOWN WINTER GARDEN!!! This be...	3 beds \| 2 baths \| 1,916 sq.ft.	$745,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 0.87% Airbnb Rental Income: $1636 Traditional Rental Income: $2484 Airbnb ROI: -1.01% Traditional ROI: 0.87%
14501 GROVE RESORT AVENUE #3406 Winter Garden, FL Attention SNOWBIRDS! Great resorts for snowbirds! Gorgeous Lakeview Condo at The Grove R...	2 beds \| 2 baths \| 1,265 sq.ft.	$204,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.08% Airbnb Rental Income: $2340 Traditional Rental Income: $2562 Airbnb ROI: -0.05% Traditional ROI: 4.08%
14501 GROVE RESORT AVENUE #1443 Winter Garden, FL GREAT NEW LISTING & PRICE: $300,000.00 MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WAT...	2 beds \| 2 baths \| 1,375 sq.ft.	$300,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 2.34% Airbnb Rental Income: $2340 Traditional Rental Income: $2726 Airbnb ROI: -1.08% Traditional ROI: 2.34%
14501 GROVE RESORT AVENUE #1220 Winter Garden, FL The Birch â 2 Bed / 2 Bath Condo-Hotel The only floorplan at The Grove with two true pr...	2 beds \| 2 baths \| 1,375 sq.ft.	$325,890	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.18% Airbnb Rental Income: $2340 Traditional Rental Income: $2792 Airbnb ROI: -0.18% Traditional ROI: 3.18%
15058 SAWGRASS BLUFF DRIVE Winter Garden, FL Under contract-accepting backup offers. Accepting Backup Offers! Location! Location! Loc...	4 beds \| 3 baths \| 2,626 sq.ft.	$579,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.43% Airbnb Rental Income: $5064 Traditional Rental Income: $3262 Airbnb ROI: 4.85% Traditional ROI: 3.43%
16707 SANCTUARY DRIVE Winter Garden, FL Welcome home to Sanctuary at Twin Waters â one of Winter Garden's most sought-after comm...	4 beds \| 3 baths \| 2,516 sq.ft.	$717,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 3.56% Airbnb Rental Income: $5064 Traditional Rental Income: $3427 Airbnb ROI: 4.47% Traditional ROI: 3.56%
14255 HAMPSHIRE BAY CIRCLE Winter Garden, FL Under contract-accepting backup offers. Virtually Staged. NEW ROOF (2025) ~ TWO NEW A/C UN...	4 beds \| 5 baths \| 4,625 sq.ft.	$1,200,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.45% Airbnb Rental Income: $5064 Traditional Rental Income: $7475 Airbnb ROI: 1.37% Traditional ROI: 4.45%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

849 SHADOWMOSS DRIVE

Winter Garden, FL

5 beds | 3 baths | 2,620 sq.ft.

$675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.87%

Airbnb Rental Income: $null

Traditional Rental Income: $3077

Airbnb ROI: N/A

Traditional ROI: 2.87%

2200 ROMANUM DRIVE

Winter Garden, FL

4 beds | 4 baths | 2,561 sq.ft.

$550,000

Airbnb cash on cash: 4.61%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $5064

Traditional Rental Income: $3451

Airbnb ROI: 4.61%

Traditional ROI: 3.48%

14411 HAMPSHIRE BAY CIRCLE

Winter Garden, FL

4 beds | 5 baths | 4,010 sq.ft.

$895,000

Airbnb cash on cash: 2.16%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $5064

Traditional Rental Income: $6971

Airbnb ROI: 2.16%

Traditional ROI: 5.69%

338 WINDFORD COURT

Winter Garden, FL

3 beds | 2 baths | 1,050 sq.ft.

$330,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1636

Traditional Rental Income: $1930

Airbnb ROI: 1.71%

Traditional ROI: 4.15%

14372 SUNBRIDGE CIRCLE

Winter Garden, FL

4 beds | 5 baths | 3,468 sq.ft.

$745,000

Airbnb cash on cash: 3.64%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $5064

Traditional Rental Income: $5980

Airbnb ROI: 3.64%

Traditional ROI: 6.44%

2202 ROMANUM DRIVE

Winter Garden, FL

3 beds | 2 baths | 1,889 sq.ft.

$565,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $1636

Traditional Rental Income: $2435

Airbnb ROI: -0.07%

Traditional ROI: 2.32%

14645 TULLAMORE LOOP

Winter Garden, FL

3 beds | 2 baths | 1,703 sq.ft.

$455,000

Airbnb cash on cash: 0.55%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $1636

Traditional Rental Income: $2276

Airbnb ROI: 0.55%

Traditional ROI: 3.13%

897 LANDRUM DRIVE

Winter Garden, FL

4 beds | 4 baths | 3,012 sq.ft.

$899,900

Airbnb cash on cash: 2.73%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $5064

Traditional Rental Income: $3383

Airbnb ROI: 2.73%