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 373 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
14411 HAMPSHIRE BAY CircleWinter Garden, FLNestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers... |
4 beds | 5 baths | 4,010 sq.ft. |
$870,000 |
Airbnb cash on cash: 1.43%
|
427 TIERRA VERDE LaneWinter 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%
|
14418 AVENUE OF THE RUSHESWinter Garden, FLWelcome to this exceptional 5-bedroom, 3 full bathroom and 1 half bathroom two-story home ... |
5 beds | 4 baths | 3,438 sq.ft. |
$810,000 |
Airbnb cash on cash: -1.4%
|
338 WINDFORD CourtWinter 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 DriveWinter 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 DriveWinter Garden, FLSpacious single-story living in the heart of Horizon West! Offering 2,571 square feet, thi... |
3 beds | 3 baths | 2,571 sq.ft. |
$674,999 |
Airbnb cash on cash: -1.42%
|
9561 WATERWAY PASSAGE DriveWinter Garden, FLSeller to contribute $5,000 credit towards Buyers closing costs. Designed for comfortable ... |
4 beds | 4 baths | 3,267 sq.ft. |
$720,000 |
Airbnb cash on cash: 2.55%
|
7179 SPRING PARK DriveWinter Garden, FLLocated in the vibrant Lakeview Pointe community within Horizon West, this model-like 4-be... |
4 beds | 3 baths | 2,272 sq.ft. |
$535,000 |
Airbnb cash on cash: 3.96%
|
5887 CYPRESS HILL RoadWinter Garden, FLWelcome to 5887 Cypress Hill Rd, a beautifully maintained 3-bedroom, 2.5-bath home located... |
3 beds | 3 baths | 1,810 sq.ft. |
$475,000 |
Airbnb cash on cash: -1.12%
|
13536 SUNSET LAKES CircleWinter 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: -1.37%
|
13377 LAKE BUTLER BoulevardWinter Garden, FLPre-Construction. To be built. To be Built, Rendering provided by master custom home build... |
5 beds | 6 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 | 4 baths | 2,876 sq.ft. |
$849,900 |
Airbnb cash on cash: 1.57%
|
735 HURLEY DriveWinter Garden, FLSingle family residence |
3 beds | 2 baths | 1,767 sq.ft. |
$489,000 |
Airbnb cash on cash: -0.44%
|
14048 LARKSPUR LAKE DriveWinter 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. |
$1,395,000 |
Airbnb cash on cash: 0.32%
|
14704 SETON CREEK BoulevardWinter Garden, FLWelcome to resort-style living in the highly sought-after Watermark community of Winter Ga... |
4 beds | 3 baths | 1,877 sq.ft. |
$525,000 |
Airbnb cash on cash: 3.86%
|
420 E CYPRESS StreetWinter 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%
|
8721 BAYVIEW CROSSING DriveWinter Garden, FLA second chance opportunity to own this exceptional home! Back on the market through no fa... |
4 beds | 4 baths | 2,842 sq.ft. |
$679,000 |
Airbnb cash on cash: 2.39%
|
15852 SHOREBIRD LaneWinter Garden, FLUnder contract-accepting backup offers. Stunning 2-Story Home in Winter Garden - 4 Bedroom... |
4 beds | 5 baths | 2,766 sq.ft. |
$799,000 |
Airbnb cash on cash: 1.47%
|
1701 E BAY StreetWinter 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 CircleWinter Garden, FLA 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: -1.48%
|
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%
|
1009 SPRING LOOP WayWinter Garden, FLWelcome to a home where the Florida lifestyle takes center stage. Tucked within the establ... |
3 beds | 2 baths | 1,497 sq.ft. |
$475,000 |
Airbnb cash on cash: -0.24%
|
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%
|
17307 BAL HARBOUR DriveWinter Garden, FLStone-and-stucco Mediterranean elevation on a paver driveway welcomes you into this beauti... |
3 beds | 2 baths | 2,123 sq.ft. |
$660,000 |
Airbnb cash on cash: -0.74%
|
20 E DIVISION StreetWinter Garden, FLAppraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformation... |
4 beds | 3 baths | 2,729 sq.ft. |
$1,080,000 |
Airbnb cash on cash: 1.6%
|
932 LOST GROVE CircleWinter Garden, FLA home that's finally been paid attention to. Four bedrooms, two-and-a-half baths, 2,891 s... |
4 beds | 3 baths | 2,891 sq.ft. |
$619,000 |
Airbnb cash on cash: 2.99%
|
6323 HAMLIN RESERVE BoulevardWinter Garden, FLLooking for a move in ready home in Hamlin, Winter Garden with a spacious private backyard... |
3 beds | 3 baths | 2,177 sq.ft. |
$549,000 |
Airbnb cash on cash: -1.9%
|
16707 SANCTUARY DriveWinter Garden, FLWelcome home to Sanctuary at Twin Waters - one of Winter Garden's most sought-after commun... |
4 beds | 3 baths | 2,516 sq.ft. |
$700,000 |
Airbnb cash on cash: 3.59%
|
15594 SHOREBIRD LaneWinter Garden, FLOne 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%
|
15187 HARROWGATE WayWinter Garden, FLLocation! 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%
|
16802 OAKBORO StreetWinter Garden, FLWelcome 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%
|