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 551 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
14411 Hampshire Bay Cir Winter Garden, FL Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers...	4 beds \| 3 baths \| 4,010 sq.ft.	$870,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 5.88% Airbnb Rental Income: $4271 Traditional Rental Income: $6971 Airbnb ROI: 1.43% Traditional ROI: 5.88%
427 Tierra Verde Ln Winter Garden, FL Virtually Staged. Welcome to this beautifully maintained custom home located in the gated ...	4 beds \| 3 baths \| 2,368 sq.ft.	$849,988	Airbnb cash on cash: 1.89% Traditional cash on cash: 1.31% Airbnb Rental Income: $4271 Traditional Rental Income: $2908 Airbnb ROI: 1.89% Traditional ROI: 1.31%
338 Windford Ct 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.	$325,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 4.23% Airbnb Rental Income: $1303 Traditional Rental Income: $1930 Airbnb ROI: 0.85% Traditional ROI: 4.23%
2628 Balforn Tower Way Winter Garden, FL Welcome to Stoneybrook West, a gated golf and recreation community in Winter Garden! This ...	3 beds \| 2 baths \| 1,372 sq.ft.	$438,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 2.05% Airbnb Rental Income: $1303 Traditional Rental Income: $2051 Airbnb ROI: -0.76% Traditional ROI: 2.05%
2202 Romanum Dr Winter Garden, FL Upgraded Turnkey Furnished Welcome to your next home in the heart of Winter Garden-whe...	3 beds \| 2 baths \| 1,889 sq.ft.	$540,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 2.47% Airbnb Rental Income: $1303 Traditional Rental Income: $2435 Airbnb ROI: -0.58% Traditional ROI: 2.47%
15725 Sweet Limetta Dr Winter Garden, FL Spacious single-story living in the heart of Horizon West! Offering 2,571 square feet, thi...	3 beds \| 2 baths \| 2,571 sq.ft.	$674,999	Airbnb cash on cash: -1.42% Traditional cash on cash: 1.98% Airbnb Rental Income: $1303 Traditional Rental Income: $3042 Airbnb ROI: -1.42% Traditional ROI: 1.98%
9561 Waterway Passage Dr Winter Garden, FL Seller to contribute $5,000 credit towards Buyers closing costs. Designed for comfortable ...	4 beds \| 3 baths \| 3,267 sq.ft.	$708,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 4.13% Airbnb Rental Income: $4271 Traditional Rental Income: $4432 Airbnb ROI: 2.55% Traditional ROI: 4.13%
7179 Spring Park Dr Winter Garden, FL Located in the vibrant Lakeview Pointe community within Horizon West, this model-like 4-be...	4 beds \| 2 baths \| 2,272 sq.ft.	$535,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 2.15% Airbnb Rental Income: $4271 Traditional Rental Income: $2467 Airbnb ROI: 3.96% Traditional ROI: 2.15%
13536 Sunset Lakes Cir Winter Garden, FL Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes com...	5 beds \| 4 baths \| 3,389 sq.ft.	$989,900	Airbnb cash on cash: 2.53% Traditional cash on cash: 4.48% Airbnb Rental Income: $5545 Traditional Rental Income: $6227 Airbnb ROI: 2.53% Traditional ROI: 4.48%
13377 Lake Butler Blvd Winter Garden, FL Pre-Construction. To be built. To be Built, Rendering provided by master custom home build...	5 beds \| 4 baths \| 6,000 sq.ft.	$5,995,000	Airbnb cash on cash: -1.32% Traditional cash on cash: -0.19% Airbnb Rental Income: $1240 Traditional Rental Income: $7090 Airbnb ROI: -1.32% Traditional ROI: -0.19%
14776 Magnolia Ridge Loop Winter Garden, FL Welcome to your Dream home with a private Pool, located in Orchard Hills Community! This s...	4 beds \| 3 baths \| 2,876 sq.ft.	$839,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 1.88% Airbnb Rental Income: $4271 Traditional Rental Income: $3622 Airbnb ROI: 1.57% Traditional ROI: 1.88%
735 Hurley Dr Winter Garden, FL Single family residence	3 beds \| 2 baths \| 1,767 sq.ft.	$489,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 2.8% Airbnb Rental Income: $1144 Traditional Rental Income: $2427 Airbnb ROI: -0.84% Traditional ROI: 2.8%
14048 Larkspur Lake Dr Winter Garden, FL Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and p...	4 beds \| 3 baths \| 2,464 sq.ft.	$1,295,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 0.42% Airbnb Rental Income: $4271 Traditional Rental Income: $3499 Airbnb ROI: 0.32% Traditional ROI: 0.42%
14704 Seton Creek Blvd Winter Garden, FL Welcome to resort-style living in the highly sought-after Watermark community of Winter Ga...	4 beds \| 2 baths \| 1,877 sq.ft.	$505,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 2.34% Airbnb Rental Income: $4271 Traditional Rental Income: $2625 Airbnb ROI: 3.86% Traditional ROI: 2.34%
420 E Cypress St Winter Garden, FL Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on ...	3 beds \| 2 baths \| 1,616 sq.ft.	$410,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 4.41% Airbnb Rental Income: $1303 Traditional Rental Income: $2686 Airbnb ROI: -0.24% Traditional ROI: 4.41%
1701 E Bay St 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.	$289,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 3.97% Airbnb Rental Income: $1522 Traditional Rental Income: $1685 Airbnb ROI: 1.75% Traditional ROI: 3.97%
1112 JUNIPER HAMMOCK Court Winter Garden, FL One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-b...	4 beds \| 2 baths \| 2,545 sq.ft.	$505,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 4.11% Airbnb Rental Income: $4271 Traditional Rental Income: $3154 Airbnb ROI: 4.57% Traditional ROI: 4.11%
13542 Sunset Lakes Cir Winter Garden, FL A New Standard of Luxury...Welcome to 13542 Sunset Lakes Circle, the 5,450 square foot cro...	5 beds \| 5 baths \| 5,450 sq.ft.	$3,799,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 1.24% Airbnb Rental Income: $1240 Traditional Rental Income: $10412 Airbnb ROI: -1.48% Traditional ROI: 1.24%
2017 Portcastle Cir Winter Garden, FL Location, location, location! Great opportunity to purchase a two-story 3/2.5 with a loft ...	3 beds \| 2 baths \| 1,857 sq.ft.	$417,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 3.67% Airbnb Rental Income: $1303 Traditional Rental Income: $2521 Airbnb ROI: -0.56% Traditional ROI: 3.67%
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: 1.36% Traditional cash on cash: 4.48% Airbnb Rental Income: $1522 Traditional Rental Income: $1916 Airbnb ROI: 1.36% 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.	$515,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 1.87% Airbnb Rental Income: $4271 Traditional Rental Income: $2376 Airbnb ROI: 3.94% Traditional ROI: 1.87%
17307 Bal Harbour Dr Winter Garden, FL Stone-and-stucco Mediterranean elevation on a paver driveway welcomes you into this beauti...	3 beds \| 2 baths \| 2,123 sq.ft.	$639,900	Airbnb cash on cash: -0.74% Traditional cash on cash: 1.99% Airbnb Rental Income: $1303 Traditional Rental Income: $2574 Airbnb ROI: -0.74% Traditional ROI: 1.99%
20 E Division St Winter Garden, FL Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformation...	4 beds \| 3 baths \| 2,729 sq.ft.	$995,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 1.49% Airbnb Rental Income: $4271 Traditional Rental Income: $3262 Airbnb ROI: 1.6% Traditional ROI: 1.49%
932 Lost Grove Cir Winter Garden, FL A home that's finally been paid attention to. Four bedrooms, two-and-a-half baths, 2,891 s...	4 beds \| 2 baths \| 2,891 sq.ft.	$619,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.46% Airbnb Rental Income: $4271 Traditional Rental Income: $3064 Airbnb ROI: 2.99% Traditional ROI: 2.46%
6323 Hamlin Reserve Blvd Winter Garden, FL Looking for a move in ready home in Hamlin, Winter Garden with a spacious private backyard...	3 beds \| 2 baths \| 2,177 sq.ft.	$549,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 2.14% Airbnb Rental Income: $1303 Traditional Rental Income: $2966 Airbnb ROI: -1.9% Traditional ROI: 2.14%
16707 Sanctuary Dr Winter Garden, FL Welcome home to Sanctuary at Twin Waters - one of Winter Garden's most sought-after commun...	4 beds \| 3 baths \| 2,516 sq.ft.	$695,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 3.67% Airbnb Rental Income: $4271 Traditional Rental Income: $3427 Airbnb ROI: 3.59% Traditional ROI: 3.67%
15594 SHOREBIRD Lane Winter Garden, FL One or more photo(s) has been virtually staged. EXPERIENCE ELEVATED LAKEFRONT LIVING IN TH...	4 beds \| 4 baths \| 3,022 sq.ft.	$1,219,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 0.76% Airbnb Rental Income: $4271 Traditional Rental Income: $4140 Airbnb ROI: 0.08% Traditional ROI: 0.76%
15187 Harrowgate Way Winter Garden, FL Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home locate...	3 beds \| 2 baths \| 1,296 sq.ft.	$425,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 3.38% Airbnb Rental Income: $1303 Traditional Rental Income: $2425 Airbnb ROI: -0.46% Traditional ROI: 3.38%
16802 Oakboro St Winter Garden, FL Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional ext...	3 beds \| 2 baths \| 1,705 sq.ft.	$485,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 2.97% Airbnb Rental Income: $1303 Traditional Rental Income: $2853 Airbnb ROI: -1.34% Traditional ROI: 2.97%
10439 Austrina Oak Loop Winter Garden, FL PRICE IMPROVEMENT + $10,000 BUYER INCENTIVE! Seller is offering up to $10,000 toward buyer...	3 beds \| 2 baths \| 2,082 sq.ft.	$549,900	Airbnb cash on cash: -1.18% Traditional cash on cash: 2.97% Airbnb Rental Income: $1303 Traditional Rental Income: $3028 Airbnb ROI: -1.18% Traditional ROI: 2.97%
368 N Boyd St Winter Garden, FL This Downtown Winter Garden stunner has continued to evolve with thoughtful, high-value up...	4 beds \| 2 baths \| 2,331 sq.ft.	$849,900	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.2% Airbnb Rental Income: $4271 Traditional Rental Income: $3380 Airbnb ROI: 2.18% Traditional ROI: 2.2%
13527 Fox Glove St Winter Garden, FL Some photos are virtually staged. Video tour available. This home has a full-home SOLAR ...	4 beds \| 3 baths \| 3,255 sq.ft.	$699,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 1.84% Airbnb Rental Income: $4271 Traditional Rental Income: $3132 Airbnb ROI: 2.21% Traditional ROI: 1.84%
16394 Taliesin St Winter Garden, FL Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lake...	5 beds \| 4 baths \| 3,093 sq.ft.	$890,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 3.61% Airbnb Rental Income: $1240 Traditional Rental Income: $5207 Airbnb ROI: -1.66% Traditional ROI: 3.61%
3387 BUOY Circle Winter Garden, FL Lake front!!!! Welcome to 3387 Buoy Cir, a beautifully maintained home located in the desi...	5 beds \| 5 baths \| 3,974 sq.ft.	$1,999,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 0.57% Airbnb Rental Income: $1240 Traditional Rental Income: $4435 Airbnb ROI: -1.37% Traditional ROI: 0.57%
16012 MICELLI Drive Winter Garden, FL Welcome to this beautifully designed 2021-built 4-bedroom, 3-bathroom plus a bonus room co...	4 beds \| 3 baths \| 2,248 sq.ft.	$599,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 3.54% Airbnb Rental Income: $4271 Traditional Rental Income: $3463 Airbnb ROI: 3.37% Traditional ROI: 3.54%
13978 Lanyard Way Winter Garden, FL Seller is offering $10k towards the buyers rate buy-down! Experience elevated Florida livi...	5 beds \| 4 baths \| 3,687 sq.ft.	$879,900	Airbnb cash on cash: -1.87% Traditional cash on cash: 2.79% Airbnb Rental Income: $1240 Traditional Rental Income: $4667 Airbnb ROI: -1.87% Traditional ROI: 2.79%
15161 Canoe Pl Winter Garden, FL OVERSIZED CORNER LOT - 3-CAR GARAGE - NEW OUTDOOR GOURMET AREA - FIRST-FLOOR SUITE - HUGE ...	5 beds \| 4 baths \| 3,816 sq.ft.	$1,070,000	Airbnb cash on cash: -1.9% Traditional cash on cash: 3.06% Airbnb Rental Income: $1240 Traditional Rental Income: $5787 Airbnb ROI: -1.9% Traditional ROI: 3.06%
16968 Hamlin Oasis Loop Winter Garden, FL Welcome to this beautiful like-new residence in the highly desirable Hamlin Pointe communi...	4 beds \| 3 baths \| 2,088 sq.ft.	$570,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.82% Airbnb Rental Income: $4271 Traditional Rental Income: $3128 Airbnb ROI: 4.28% Traditional ROI: 3.82%
2450 Dahlgren Way Winter Garden, FL Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-...	5 beds \| 5 baths \| 4,365 sq.ft.	$1,499,990	Airbnb cash on cash: -1.22% Traditional cash on cash: 3.14% Airbnb Rental Income: $1240 Traditional Rental Income: $7419 Airbnb ROI: -1.22% Traditional ROI: 3.14%
7701 Summerlake Pointe Blvd Winter Garden, FL Experience of luxury living in this 2021 custom-built contemporary masterpiece by Davila H...	5 beds \| 5 baths \| 4,072 sq.ft.	$2,150,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.2% Airbnb Rental Income: $1240 Traditional Rental Income: $8202 Airbnb ROI: -1.49% Traditional ROI: 2.2%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Garden, FL

14411 Hampshire Bay Cir

Winter Garden, FL

4 beds | 3 baths | 4,010 sq.ft.

$870,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: 5.88%

Airbnb Rental Income: $4271

Traditional Rental Income: $6971

Airbnb ROI: 1.43%

Traditional ROI: 5.88%

427 Tierra Verde Ln

Winter Garden, FL

4 beds | 3 baths | 2,368 sq.ft.

$849,988

Airbnb cash on cash: 1.89%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $4271

Traditional Rental Income: $2908

Airbnb ROI: 1.89%

Traditional ROI: 1.31%

338 Windford Ct

Winter Garden, FL

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

$325,000

Airbnb cash on cash: 0.85%

Traditional cash on cash: 4.23%

Airbnb Rental Income: $1303

Traditional Rental Income: $1930

Airbnb ROI: 0.85%

Traditional ROI: 4.23%

2628 Balforn Tower Way

Winter Garden, FL

3 beds | 2 baths | 1,372 sq.ft.

$438,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1303

Traditional Rental Income: $2051

Airbnb ROI: -0.76%

Traditional ROI: 2.05%

2202 Romanum Dr

Winter Garden, FL

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

$540,000

Airbnb cash on cash: -0.58%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1303

Traditional Rental Income: $2435

Airbnb ROI: -0.58%

Traditional ROI: 2.47%

15725 Sweet Limetta Dr

Winter Garden, FL

3 beds | 2 baths | 2,571 sq.ft.

$674,999

Airbnb cash on cash: -1.42%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $1303

Traditional Rental Income: $3042

Airbnb ROI: -1.42%

Traditional ROI: 1.98%

9561 Waterway Passage Dr

Winter Garden, FL

4 beds | 3 baths | 3,267 sq.ft.

$708,000

Airbnb cash on cash: 2.55%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $4271

Traditional Rental Income: $4432

Airbnb ROI: 2.55%

Traditional ROI: 4.13%

7179 Spring Park Dr

Winter Garden, FL

4 beds | 2 baths | 2,272 sq.ft.

$535,000

Airbnb cash on cash: 3.96%

Traditional cash on cash: 2.15%

Airbnb Rental Income: $4271

Traditional Rental Income: $2467

Airbnb ROI: 3.96%