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 One or more photo(s) has been virtually staged. Prime Winter Garden Location \| Westfield L...	5 beds \| 3 baths \| 2,620 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $3077 Airbnb ROI: N/A Traditional ROI: 2.48%
13728 Fox Glove St Winter Garden, FL Short Sale. Short Sale--AS IS4 bedroom, 2 1/2 baths pool home in Stoneybrook West Comm...	5 beds \| 3 baths \| 3,391 sq.ft.	$739,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $3736 Airbnb ROI: N/A Traditional ROI: 3.04%
7189 SUMMERLAKE GROVES STREET Winter Garden, FL COME set your eyes on your Gorgeous 2-Story Winter Garden DREAM HOME located in the Highla...	3 beds \| 3 baths \| 2,138 sq.ft.	$609,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.22% Airbnb Rental Income: $1636 Traditional Rental Income: $3295 Airbnb ROI: -0.5% Traditional ROI: 3.22%
13836 Daniels Landing Cir Winter Garden, FL HOT PROPERTY! Only Townhome available for sale in BEAUTIFUL and desirable Daniels Landing...	2 beds \| 2 baths \| 1,234 sq.ft.	$300,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 2.63% Airbnb Rental Income: $2340 Traditional Rental Income: $1660 Airbnb ROI: 2.98% Traditional ROI: 2.63%
15140 SUNRISE GROVE COURT Winter Garden, FL Under contract-accepting backup offers. Imagine a life where lakeside serenity meets moder...	3 beds \| 3 baths \| 2,012 sq.ft.	$390,987	Airbnb cash on cash: -0.74% Traditional cash on cash: 5.07% Airbnb Rental Income: $1636 Traditional Rental Income: $3302 Airbnb ROI: -0.74% Traditional ROI: 5.07%
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%
16197 Wind View Ln Winter Garden, FL Welcome to Waterleigh-Marina Bay! This quiet & lovely neighborhood is beautifully maintain...	3 beds \| 2 baths \| 2,027 sq.ft.	$527,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.19% Airbnb Rental Income: $1636 Traditional Rental Income: $2962 Airbnb ROI: -0.44% Traditional ROI: 3.19%
264 BLUE STONE CIRCLE Winter Garden, FL LOCATION, LOCATION, LOCATION! Welcome to 264 Blue Stone Cir in the highly desirable Winter...	4 beds \| 3 baths \| 2,538 sq.ft.	$725,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 3.53% Airbnb Rental Income: $5064 Traditional Rental Income: $3698 Airbnb ROI: 4.02% Traditional ROI: 3.53%
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.	$585,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.21% Airbnb Rental Income: $1636 Traditional Rental Income: $2435 Airbnb ROI: -0.1% Traditional ROI: 2.21%
16232 ROCK COAST DRIVE Winter Garden, FL Under contract-accepting backup offers. Welcome to your dream home and backyard oasis! Thi...	4 beds \| 5 baths \| 3,491 sq.ft.	$925,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.22% Airbnb Rental Income: $5064 Traditional Rental Income: $7312 Airbnb ROI: 2.41% Traditional ROI: 6.22%
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%
15558 Sandfield Loop Winter Garden, FL NEW PRICE MAKES THIS THE BEST DEAL ON THE BLOCK! This one will check ALL your boxes...Tayl...	4 beds \| 3 baths \| 4,307 sq.ft.	$765,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 2.23% Airbnb Rental Income: $5064 Traditional Rental Income: $3134 Airbnb ROI: 3.49% Traditional ROI: 2.23%
2154 OAKINGTON STREET Winter Garden, FL Welcome to this beautifully maintained, single-story home that perfectly blends comfort, s...	3 beds \| 2 baths \| 1,585 sq.ft.	$469,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.23% Airbnb Rental Income: $1636 Traditional Rental Income: $2263 Airbnb ROI: -0.25% Traditional ROI: 2.23%
14844 Driftwater Dr Winter Garden, FL Come see this gorgeous 2016 Lennar built, 4 bedroom 2.5 bathroom, 2,000 sq ft townhome in ...	4 beds \| 2 baths \| 1,990 sq.ft.	$429,990	Airbnb cash on cash: 6.69% Traditional cash on cash: 2.53% Airbnb Rental Income: $5064 Traditional Rental Income: $2356 Airbnb ROI: 6.69% Traditional ROI: 2.53%
14501 GROVE RESORT AVENUE #1111 Winter Garden, FL Ground Floor Unit \| Pond and Fountain Views \| Aggressively Priced Ground floor residence f...	2 beds \| 2 baths \| 1,265 sq.ft.	$205,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.98% Airbnb Rental Income: $2340 Traditional Rental Income: $2636 Airbnb ROI: -0.51% Traditional ROI: 3.98%
897 LANDRUM DRIVE Winter Garden, FL Welcome to one of Winter Garden's most coveted addresses â nestled in the heart of the G...	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%
9338 Tyrella Pine Trl Winter Garden, FL You will love this beautiful 4 bedrooms, 2.5 bathrooms, 2 car garage home located in the d...	4 beds \| 2 baths \| 1,696 sq.ft.	$449,000	Airbnb cash on cash: 7.75% Traditional cash on cash: 4.89% Airbnb Rental Income: $5064 Traditional Rental Income: $2829 Airbnb ROI: 7.75% Traditional ROI: 4.89%
14282 CREEKBED CIRCLE Winter Garden, FL *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing co...	4 beds \| 4 baths \| 3,479 sq.ft.	$924,500	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.61% Airbnb Rental Income: $5064 Traditional Rental Income: $5782 Airbnb ROI: 2.57% Traditional ROI: 4.61%
604 FOSTER AVENUE Winter Garden, FL Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart Dis...	3 beds \| 2 baths \| 1,275 sq.ft.	$400,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.92% Airbnb Rental Income: $1636 Traditional Rental Income: $2092 Airbnb ROI: 1.48% Traditional ROI: 3.92%
1672 Malcolm Pointe Dr Winter Garden, FL Charming 3BD/2BA HOME sits on 1/4 ACRE LOT in a quiet CUL-DE-SAC with a NEW ROOF (2021), N...	3 beds \| 2 baths \| 2,035 sq.ft.	$509,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.94% Airbnb Rental Income: $1636 Traditional Rental Income: $2311 Airbnb ROI: 0.56% Traditional ROI: 2.94%
7832 Freestyle Ln Winter Garden, FL BETTER THAN NEW and less than 1 year old. Ideal MODERN one story floor plan with all the r...	4 beds \| 3 baths \| 2,650 sq.ft.	$1,075,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3030 Airbnb ROI: 2.44% Traditional ROI: 1.44%
261 Zachary Wade St Winter Garden, FL *** Multiple offers received, deadline for highest and best is Wednesday 06/01/2022 @ 10am...	4 beds \| 3 baths \| 3,728 sq.ft.	$1,699,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 0.65% Airbnb Rental Income: $5064 Traditional Rental Income: $3554 Airbnb ROI: 0.96% Traditional ROI: 0.65%
14501 Grove Resort Ave #1732 Winter Garden, FL The Grove Resort & Spa is the perfect Orlando's vacation and family resort destination for...	2 beds \| 2 baths \| 1,265 sq.ft.	$189,950	Airbnb cash on cash: 1.34% Traditional cash on cash: 5.08% Airbnb Rental Income: $2340 Traditional Rental Income: $2436 Airbnb ROI: 1.34% Traditional ROI: 5.08%
13536 SUNSET LAKES CIRCLE 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.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $6227 Airbnb ROI: N/A Traditional ROI: 3.72%
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%
10007 Little Alcove Loop Winter Garden, FL Don't wait to build new- enjoy the upgraded finishes in this Emerald Home now! Beautifully...	4 beds \| 3 baths \| 2,921 sq.ft.	$999,990	Airbnb cash on cash: 2.84% Traditional cash on cash: 2.49% Airbnb Rental Income: $5064 Traditional Rental Income: $3702 Airbnb ROI: 2.84% Traditional ROI: 2.49%
14501 Grove Resort Ave #1503 Winter Garden, FL Own, Earn and Enjoy at one of the World's Premier Vacation destinations, The Grove Resort ...	3 beds \| 2 baths \| 1,396 sq.ft.	$285,000	Airbnb cash on cash: -3.03% Traditional cash on cash: 1.96% Airbnb Rental Income: $1636 Traditional Rental Income: $2515 Airbnb ROI: -3.03% Traditional ROI: 1.96%
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%
9355 Tyrella Pine Trl Winter Garden, FL This Winter Garden two-story home offers a den, kitchen quartz countertops, stainless stee...	3 beds \| 2 baths \| 1,670 sq.ft.	$475,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.76% Airbnb Rental Income: $1636 Traditional Rental Income: $2250 Airbnb ROI: 0.34% Traditional ROI: 2.76%
14447 PRUNNINGWOOD PLACE Winter Garden, FL One or more photo(s) has been virtually staged. This stylish townhome in the highly sought...	2 beds \| 3 baths \| 1,250 sq.ft.	$340,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.01% Airbnb Rental Income: $2340 Traditional Rental Income: $2464 Airbnb ROI: 1.81% Traditional ROI: 4.01%
15508 PEBBLE RIDGE STREET Winter Garden, FL This is the one youâve been waiting for. A beautifully maintained four bedroom pool home...	4 beds \| 3 baths \| 2,763 sq.ft.	$695,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.14% Airbnb Rental Income: $5064 Traditional Rental Income: $3612 Airbnb ROI: 3.79% Traditional ROI: 3.14%
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.	$475,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.21% Airbnb Rental Income: $1636 Traditional Rental Income: $3086 Airbnb ROI: -0.09% Traditional ROI: 4.21%
705 Garden West Ter Winter Garden, FL New Construction by custom builder. Enjoy TRAILSIDE living at it's finest! Garden West is ...	4 beds \| 3 baths \| 2,698 sq.ft.	$1,350,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 0.2% Airbnb Rental Income: $5064 Traditional Rental Income: $2963 Airbnb ROI: 1.05% Traditional ROI: 0.2%
9803 Amber Chestnut Way Winter Garden, FL An incredible energy-efficient Townhouse with a Turnkey package! A Corner Lot Residence wi...	4 beds \| 3 baths \| 2,303 sq.ft.	$535,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 2.62% Airbnb Rental Income: $5064 Traditional Rental Income: $2805 Airbnb ROI: 5.07% Traditional ROI: 2.62%
225 Southern Pecan Cir #208 Winter Garden, FL Great Investment property 2 Bedroom 2 Bathroom Condominium in the community of Southern pi...	2 beds \| 2 baths \| 1,264 sq.ft.	$289,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 2.88% Airbnb Rental Income: $2340 Traditional Rental Income: $1872 Airbnb ROI: 2.47% Traditional ROI: 2.88%
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.	$465,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.68% Airbnb Rental Income: $1636 Traditional Rental Income: $2487 Airbnb ROI: -0.33% Traditional ROI: 2.68%
1646 Holcomb Creek St Winter Garden, FL LOOK NO MORE! This is one of the most spectacular and energy efficient Meritage Home's fl...	4 beds \| 4 baths \| 3,841 sq.ft.	$929,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 3.32% Airbnb Rental Income: $5064 Traditional Rental Income: $4609 Airbnb ROI: 2.65% Traditional ROI: 3.32%
16137 Wind View Ln Winter Garden, FL DON'T WAIT FOR A NEW BUILT, WHEN YOU CAN PURCHASE THIS AMAZING HOME THAT JUST HIT THE MARK...	4 beds \| 3 baths \| 2,477 sq.ft.	$565,000	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.44% Airbnb Rental Income: $5064 Traditional Rental Income: $3707 Airbnb ROI: 5.05% Traditional ROI: 4.44%
16029 Tollington Aly Winter Garden, FL This beautiful MODEL HOME WITH LEASEBACK delivers 3 beds, 2.5 bath, and a 2-car alley-load...	3 beds \| 2 baths \| 2,341 sq.ft.	$619,500	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.85% Airbnb Rental Income: $1636 Traditional Rental Income: $2597 Airbnb ROI: 0.38% Traditional ROI: 2.85%

Real Estate investment in Winter-garden, FL

There are 976 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $625,580 and the average price per square foot is $259. In May 2026, the average monthly cash on cash return in Winter Garden is 3.00%. The average monthly rental income in Winter Garden is $2,900.

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

There are 976 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 $2,900.

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.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.48%

Airbnb Rental Income: $null

Traditional Rental Income: $3077

Airbnb ROI: N/A

Traditional ROI: 2.48%

13728 Fox Glove St

Winter Garden, FL

5 beds | 3 baths | 3,391 sq.ft.

$739,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3736

Airbnb ROI: N/A

Traditional ROI: 3.04%

7189 SUMMERLAKE GROVES STREET

Winter Garden, FL

3 beds | 3 baths | 2,138 sq.ft.

$609,999

Airbnb cash on cash: -0.5%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $1636

Traditional Rental Income: $3295

Airbnb ROI: -0.5%

Traditional ROI: 3.22%

13836 Daniels Landing Cir

Winter Garden, FL

2 beds | 2 baths | 1,234 sq.ft.

$300,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2340

Traditional Rental Income: $1660

Airbnb ROI: 2.98%

Traditional ROI: 2.63%

15140 SUNRISE GROVE COURT

Winter Garden, FL

3 beds | 3 baths | 2,012 sq.ft.

$390,987

Airbnb cash on cash: -0.74%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1636

Traditional Rental Income: $3302

Airbnb ROI: -0.74%

Traditional ROI: 5.07%

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%

16197 Wind View Ln

Winter Garden, FL

3 beds | 2 baths | 2,027 sq.ft.

$527,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1636

Traditional Rental Income: $2962

Airbnb ROI: -0.44%

Traditional ROI: 3.19%

264 BLUE STONE CIRCLE

Winter Garden, FL

4 beds | 3 baths | 2,538 sq.ft.

$725,000

Airbnb cash on cash: 4.02%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $5064

Traditional Rental Income: $3698

Airbnb ROI: 4.02%