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.

Investment Property for Sale in Winter Garden, FL

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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%
1437 SCARLET OAK LOOP Winter Garden, FL Don't miss this opportunity to own a well-maintained townhome in the sought-after gated co...	3 beds \| 3 baths \| 1,684 sq.ft.	$350,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 4.12% Airbnb Rental Income: $1636 Traditional Rental Income: $2409 Airbnb ROI: 0.36% Traditional ROI: 4.12%
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: 4.82% Traditional cash on cash: 5.54% Airbnb Rental Income: $2340 Traditional Rental Income: $1885 Airbnb ROI: 4.82% Traditional ROI: 5.54%
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%
14501 GROVE RESORT AVENUE #1111 Winter Garden, FL 14K PRICE DROP \| Ground Floor Unit \| Pond and Fountain Views \| Aggressively Priced Ground ...	2 beds \| 2 baths \| 1,265 sq.ft.	$189,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 4.4% Airbnb Rental Income: $2340 Traditional Rental Income: $2636 Airbnb ROI: -0.47% Traditional ROI: 4.4%
7279 DUXBURY LANE Winter Garden, FL Welcome to this beautifully maintained END-UNIT townhome in Lakeview Pointe, one of Horizo...	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%
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%
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%
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%
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%
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%
648 ORANGE BELT LOOP Winter Garden, FL Under contract-accepting backup offers. Welcome to your opportunity to own in one of the m...	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%
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%
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.	$398,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 4.49% Airbnb Rental Income: $1636 Traditional Rental Income: $3164 Airbnb ROI: -0.84% Traditional ROI: 4.49%
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%
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%
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%

Real Estate investment in Winter-garden, FL

There are 542 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $609,685 and the average price per square foot is $253. In June 2026, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,926.

Winter-garden, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 542 investment properties available for sale in Winter-garden.

In 2026, the best neighborhood to buy investment property is Winter Garden.

The ROI for Long-Term is higher than the Short-Term in Winter-garden with average rental income of $2,926.

Your search for investment property begins and ends here

Investment Property 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%

1437 SCARLET OAK LOOP

Winter Garden, FL

3 beds | 3 baths | 1,684 sq.ft.

$350,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1636

Traditional Rental Income: $2409

Airbnb ROI: 0.36%

Traditional ROI: 4.12%

373 ERON WAY #47

Winter Garden, FL

2 beds | 2 baths | 840 sq.ft.

$182,000

Airbnb cash on cash: 4.82%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $2340

Traditional Rental Income: $1885

Airbnb ROI: 4.82%