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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
14411 Hampshire Bay CirWinter Garden, FLNestled 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%
|
427 Tierra Verde LnWinter Garden, FLVirtually 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%
|
27 Windtree Ln #102Winter Garden, FLWelcome 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%
|
338 Windford CtWinter Garden, FLDiscover 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%
|
2628 Balforn Tower WayWinter Garden, FLWelcome 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%
|
2202 Romanum DrWinter 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%
|
15725 Sweet Limetta DrWinter Garden, FLSpacious 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%
|
373 Eron Way #47Winter Garden, FLShort 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%
|
9561 Waterway Passage DrWinter Garden, FLSeller 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%
|
14501 Grove Resort Ave #1111Winter Garden, FLPond 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%
|
7179 Spring Park DrWinter Garden, FLLocated 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%
|
760 Walkers Grove LnWinter Garden, FLWELCOME HOME to this immaculately maintained 3-bedroom, 2.5-bath townhome with a 2-car gar... |
3 beds | 2 baths | 1,915 sq.ft. |
$540,000 |
Airbnb cash on cash: -1.48%
|
13536 Sunset Lakes CirWinter Garden, FLExperience 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%
|
13377 Lake Butler BlvdWinter Garden, FLPre-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%
|
14776 Magnolia Ridge LoopWinter Garden, FLWelcome 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%
|
735 Hurley DrWinter Garden, FLSingle family residence |
3 beds | 2 baths | 1,767 sq.ft. |
$489,000 |
Airbnb cash on cash: -0.84%
|
14048 Larkspur Lake DrWinter Garden, FLVirtually 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%
|
14501 Grove Resort Ave #3303Winter Garden, FLExperience 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%
|
14704 Seton Creek BlvdWinter Garden, FLWelcome 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%
|
14501 Grove Resort Ave #3202Winter Garden, FLWelcome 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%
|
420 E Cypress StWinter Garden, FLWelcome 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%
|
14501 Grove Resort Ave #1409Winter Garden, FLProperty 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%
|
1701 E Bay StWinter Garden, FLWelcome 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%
|
1112 JUNIPER HAMMOCK CourtWinter Garden, FLOne 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%
|
13542 Sunset Lakes CirWinter Garden, FLA 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%
|
2017 Portcastle CirWinter Garden, FLLocation, 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%
|
8873 Fountain Palm AlyWinter Garden, FLLuxury Toll Brothers End-Unit Townhome in Lakeshore Preserve! This beautifully maintained ... |
3 beds | 2 baths | 2,162 sq.ft. |
$565,000 |
Airbnb cash on cash: -1.95%
|
634 FOSTER AvenueWinter Garden, FLCharming 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%
|
131 Oak Laurel DrWinter Garden, FL131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable ... |
3 beds | 3 baths | 1,906 sq.ft. |
$799,000 |
Airbnb cash on cash: -1.95%
|
1061 PORTMOOR WayWinter Garden, FLWelcome 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%
|
10509 Spring Arbor LnWinter Garden, FLSeller is motivated! Take advantage of this incredible opportunity to own a beautifully ma... |
3 beds | 2 baths | 1,868 sq.ft. |
$439,000 |
Airbnb cash on cash: -1.44%
|
17307 Bal Harbour DrWinter Garden, FLStone-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%
|
14501 Grove Resort Ave #3535Winter Garden, FLNew 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%
|
20 E Division StWinter Garden, FLAppraisal 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%
|
14501 GROVE RESORT Avenue #1440Winter Garden, FLSeller 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%
|
14501 Grove Resort Ave #1535Winter Garden, FLGREAT 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%
|
932 Lost Grove CirWinter Garden, FLA 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%
|
14501 Grove Resort Ave #3215Winter Garden, FLLocated 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%
|
6323 Hamlin Reserve BlvdWinter Garden, FLLooking 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%
|
14501 Grove Resort Ave #1443Winter Garden, FLGREAT $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%
|
Real Estate investment in Winter-garden, FL
There are 797 properties for sale in the city of Winter Garden . The median list price in Winter Garden is $599,054 and the average price per square foot is $257. In October 2026, the average monthly cash on cash return in Winter Garden is 2.00%. The average monthly rental income in Winter Garden is $2,118.