Real Estate Investment Properties for Sale in Winter Springs, FL

Looking for investment property in Winter Springs, FL with high ROI ?

Explore a variety of short-term homes & houses in Winter Springs, FL. Invest wisely with VRBO & Winter Springs, 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 Springs, FL

Search for Single Family Residential for Sale in Winter Springs, 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 90 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
150 N EDGEMON AVENUE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ch...	3 beds \| 1 baths \| 1,008 sq.ft.	$289,999	Airbnb cash on cash: 2.44% Traditional cash on cash: 6.7% Airbnb Rental Income: $1827 Traditional Rental Income: $2498 Airbnb ROI: 2.44% Traditional ROI: 6.7%
1029 ANTELOPE TRAIL Winter Springs, FL Under contract-accepting backup offers. Located in the highly desirable Tuscawilla communi...	4 beds \| 2 baths \| 1,939 sq.ft.	$481,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.29% Airbnb Rental Income: $3833 Traditional Rental Income: $2835 Airbnb ROI: 4.66% Traditional ROI: 4.29%
710 BRIARWOOD DRIVE Winter Springs, FL Welcome to this beautifully updated 4-bedroom, 2-bath home in Winter Springs, FL, featurin...	4 beds \| 2 baths \| 1,769 sq.ft.	$375,000	Airbnb cash on cash: 5.92% Traditional cash on cash: 5.12% Airbnb Rental Income: $3833 Traditional Rental Income: $2724 Airbnb ROI: 5.92% Traditional ROI: 5.12%
1331 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL BRAND NEW tile barrel roof just installed Welcome to easy-maintenance living in the hi...	3 beds \| 2 baths \| 1,657 sq.ft.	$450,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.94% Airbnb Rental Income: $1827 Traditional Rental Income: $2776 Airbnb ROI: 0.52% Traditional ROI: 3.94%
337 KIRKCALDY DRIVE Winter Springs, FL Warm and inviting home located in the highly sought-after Highland Village community of Wi...	2 beds \| 2 baths \| 974 sq.ft.	$287,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.3% Airbnb Rental Income: $1652 Traditional Rental Income: $1943 Airbnb ROI: 2.52% Traditional ROI: 5.3%
131 LISA LOOP Winter Springs, FL Check out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly ...	4 beds \| 3 baths \| 2,309 sq.ft.	$489,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 4.39% Airbnb Rental Income: $3833 Traditional Rental Income: $3167 Airbnb ROI: 4.04% Traditional ROI: 4.39%
1201 WOLVERINE TRAIL Winter Springs, FL Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighbo...	4 beds \| 2 baths \| 1,979 sq.ft.	$500,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.93% Airbnb Rental Income: $3833 Traditional Rental Income: $2930 Airbnb ROI: 4.09% Traditional ROI: 3.93%
1340 DELANEY DRIVE Winter Springs, FL Under contract-accepting backup offers. Welcome to 1340 Delaney Drive, a move-in-ready hom...	3 beds \| 2 baths \| 1,422 sq.ft.	$265,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 7.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2558 Airbnb ROI: 2.86% Traditional ROI: 7.76%
1250 STONE HARBOUR ROAD Winter Springs, FL IMMACULATE 4 bedroom, 2 bathroom home in the beautiful GATED community of Parkstone! Loca...	4 beds \| 2 baths \| 2,113 sq.ft.	$540,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.37% Airbnb Rental Income: $3833 Traditional Rental Income: $2543 Airbnb ROI: 3.29% Traditional ROI: 2.37%
689 SEVEN OAKS BOULEVARD Winter Springs, FL Under contract-accepting backup offers. This 4 bedroom pool home has an office + a loft, t...	4 beds \| 3 baths \| 2,541 sq.ft.	$600,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.68% Airbnb Rental Income: $3833 Traditional Rental Income: $3184 Airbnb ROI: 3.36% Traditional ROI: 3.68%
613 BONITA ROAD Winter Springs, FL Tucked beneath a canopy of mature trees in one of Winter Springsâ most charming ranch-st...	4 beds \| 4 baths \| 3,281 sq.ft.	$739,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 2.63% Airbnb Rental Income: $3833 Traditional Rental Income: $3368 Airbnb ROI: 2.1% Traditional ROI: 2.63%
1106 SUPERIOR COURT Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to the highly sought-after Tuscawi...	4 beds \| 3 baths \| 2,353 sq.ft.	$625,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.87% Airbnb Rental Income: $3833 Traditional Rental Income: $3076 Airbnb ROI: 2.75% Traditional ROI: 2.87%
1010 TURKEY HOLLOW CIRCLE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 2 baths \| 1,740 sq.ft.	$505,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.91% Airbnb Rental Income: $3833 Traditional Rental Income: $2944 Airbnb ROI: 4.04% Traditional ROI: 3.91%
1163 BALTIC LANE Winter Springs, FL This lovingly maintained 4-bedroom, 2-bath home in a quiet neighborhood of sought-after Wi...	4 beds \| 2 baths \| 2,066 sq.ft.	$510,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.11% Airbnb Rental Income: $3833 Traditional Rental Income: $2630 Airbnb ROI: 3.9% Traditional ROI: 3.11%
622 ANHINGA ROAD Winter Springs, FL NEW ROOF!!! NEW ROOF!!! NEW ROOF!!! The roof is currently being replaced â what you have...	3 beds \| 3 baths \| 1,721 sq.ft.	$399,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.66% Airbnb Rental Income: $1827 Traditional Rental Income: $2709 Airbnb ROI: 0.99% Traditional ROI: 4.66%
515 SEASONS COURT Winter Springs, FL One or more photo(s) has been virtually staged.Move-In Ready Home â Fully Updated In...	3 beds \| 2 baths \| 1,101 sq.ft.	$299,900	Airbnb cash on cash: 1.84% Traditional cash on cash: 5.1% Airbnb Rental Income: $1827 Traditional Rental Income: $2253 Airbnb ROI: 1.84% Traditional ROI: 5.1%
1314 Augusta National Blvd Winter Springs, FL Pay in Bitcoin for this modern, yet cozy family home in Tuscawilla, for sale by owner! Sp...	3 beds \| 3 baths \| 2,004 sq.ft.	$600,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.23% Airbnb Rental Income: $1827 Traditional Rental Income: $2508 Airbnb ROI: 0.14% Traditional ROI: 2.23%
1300 SWIFT CREEK WAY Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to your new home at 1300 Swift Cre...	4 beds \| 3 baths \| 2,030 sq.ft.	$550,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 3.52% Airbnb Rental Income: $3833 Traditional Rental Income: $3170 Airbnb ROI: 3.2% Traditional ROI: 3.52%
1075 CONDOR PLACE Winter Springs, FL Under contract-accepting backup offers. Charming three bedroom, two full bathroom, two car...	3 beds \| 2 baths \| 1,749 sq.ft.	$414,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2667 Airbnb ROI: 1.33% Traditional ROI: 4.76%
31 S EDGEMON AVENUE Winter Springs, FL Under contract-accepting backup offers. This charming home offers a spacious floor plan wi...	4 beds \| 3 baths \| 1,270 sq.ft.	$348,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 4.17% Airbnb Rental Income: $3833 Traditional Rental Income: $2038 Airbnb ROI: 7.13% Traditional ROI: 4.17%
403 MURPHY ROAD Winter Springs, FL Welcome home to this beautiful 3 bedrooms, 2 bathrooms house with a pool. Come and enjoy t...	3 beds \| 2 baths \| 1,520 sq.ft.	$410,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 4.98% Airbnb Rental Income: $1827 Traditional Rental Income: $2883 Airbnb ROI: 0.95% Traditional ROI: 4.98%
110 MOCKINGBIRD LANE Winter Springs, FL Welcome home! This beautifully updated 4 bed, 2 bath block home sits on over Â¼ acre with ...	4 beds \| 2 baths \| 1,660 sq.ft.	$400,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 4.7% Airbnb Rental Income: $3833 Traditional Rental Income: $2774 Airbnb ROI: 5.32% Traditional ROI: 4.7%
122 STONE GABLE CIR Winter Springs, FL ELEGANT CONTEMPORARY HOUSE WELCOMES YOU THROUGH A FOYER INTO THE LIVING/DINING AREA. THE H...	3 beds \| 3 baths \| 2,147 sq.ft.	$499,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.06% Airbnb Rental Income: $1827 Traditional Rental Income: $3095 Airbnb ROI: 0.29% Traditional ROI: 4.06%
1356 VIA VILLA NOVA Winter Springs, FL Your private oasis awaits on a PREMIUM WATERFRONT LOT. Forget the stress... MOVE-IN READ...	3 beds \| 2 baths \| 1,864 sq.ft.	$499,999	Airbnb cash on cash: 1.51% Traditional cash on cash: 5.21% Airbnb Rental Income: $1827 Traditional Rental Income: $3060 Airbnb ROI: 1.51% Traditional ROI: 5.21%
1204 SWAN STREET Winter Springs, FL Great location, No HOA..69 acres , 4 bedrooms,2 bathrooms, one half bathroom out door sho...	4 beds \| 3 baths \| 3,334 sq.ft.	$750,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 4.24% Airbnb Rental Income: $3833 Traditional Rental Income: $4099 Airbnb ROI: 2.68% Traditional ROI: 4.24%
140 SEVILLE CHASE DRIVE Winter Springs, FL Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - a...	5 beds \| 4 baths \| 3,129 sq.ft.	$779,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3908 Airbnb ROI: N/A Traditional ROI: 3.22%
930 ARABIAN AVENUE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 3,522 sq.ft.	$999,900	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.73% Airbnb Rental Income: $3833 Traditional Rental Income: $3576 Airbnb ROI: 2.11% Traditional ROI: 2.73%
202 ARROWHEAD COURT Winter Springs, FL Under contract-accepting backup offers. BRAND NEW TILE ROOF! **Buyer backed out due to per...	5 beds \| 5 baths \| 4,078 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $5368 Airbnb ROI: N/A Traditional ROI: 2.26%
314 SAN GABRIEL STREET Winter Springs, FL PRICE REDUCTION: Welcome to your dream home in the highly sought-after Deer Song Communit...	3 beds \| 2 baths \| 1,091 sq.ft.	$279,990	Airbnb cash on cash: 2.38% Traditional cash on cash: 5.5% Airbnb Rental Income: $1827 Traditional Rental Income: $2157 Airbnb ROI: 2.38% Traditional ROI: 5.5%
523 SADDLEWOOD LANE Winter Springs, FL Under contract-accepting backup offers. Step through grand double doors into this beautifu...	4 beds \| 3 baths \| 2,315 sq.ft.	$575,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 4.03% Airbnb Rental Income: $3833 Traditional Rental Income: $3168 Airbnb ROI: 3.73% Traditional ROI: 4.03%
126 SEVILLE CHASE DRIVE Winter Springs, FL Welcome to Seville Chase, a quiet gated neighborhood in Winter Springs with tree-lined str...	5 beds \| 4 baths \| 3,205 sq.ft.	$785,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $3844 Airbnb ROI: N/A Traditional ROI: 2.67%
203 HERRELL ROAD Winter Springs, FL Under contract-accepting backup offers. **Seller will contribute towards buyer closing cos...	5 beds \| 4 baths \| 3,566 sq.ft.	$573,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.27% Airbnb Rental Income: $null Traditional Rental Income: $4460 Airbnb ROI: N/A Traditional ROI: 6.27%
270 SAN GABRIEL STREET Winter Springs, FL Welcome to 270 San Gabriel Street in Winter Springs, Florida â this home perfectly blend...	3 beds \| 2 baths \| 1,089 sq.ft.	$269,900	Airbnb cash on cash: 3.22% Traditional cash on cash: 6.93% Airbnb Rental Income: $1827 Traditional Rental Income: $2278 Airbnb ROI: 3.22% Traditional ROI: 6.93%
114 SUNDANCE COURT Winter Springs, FL One or more photo(s) has been virtually staged. If youâve been searching for space, loca...	4 beds \| 2 baths \| 1,356 sq.ft.	$315,500	Airbnb cash on cash: 7.09% Traditional cash on cash: 5.73% Airbnb Rental Income: $3833 Traditional Rental Income: $2602 Airbnb ROI: 7.09% Traditional ROI: 5.73%
1096 DYSON DRIVE Winter Springs, FL Welcome to 1096 Dyson Drive, a truly one-of-a-kind pool home in the heart of Winter Spring...	3 beds \| 2 baths \| 1,882 sq.ft.	$624,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 3.91% Airbnb Rental Income: $1827 Traditional Rental Income: $3179 Airbnb ROI: 0.75% Traditional ROI: 3.91%
124 BLUE CREEK DRIVE Winter Springs, FL Welcome to this 5 bedroom, 3 bathroom pool home in the highly desirable Tuskawilla neighbo...	5 beds \| 3 baths \| 2,762 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $4314 Airbnb ROI: N/A Traditional ROI: 3.81%
1225 STONE HARBOUR ROAD Winter Springs, FL Welcome to this lakefront home in the community of Parkstone. This home has private shorel...	5 beds \| 5 baths \| 3,512 sq.ft.	$780,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $5053 Airbnb ROI: N/A Traditional ROI: 4.72%
705 CRESTWOOD WAY Winter Springs, FL Welcome to this delightful one-story home in Wildwood, perfectly set on a spacious corner ...	3 beds \| 2 baths \| 1,296 sq.ft.	$319,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 5.43% Airbnb Rental Income: $1827 Traditional Rental Income: $2374 Airbnb ROI: 1.97% Traditional ROI: 5.43%
981 TUSKAWILLA TRAIL Winter Springs, FL Price Improvement! Now offered at $899,000 â Exceptional opportunity in the Tuskawilla /...	4 beds \| 3 baths \| 3,284 sq.ft.	$899,999	Airbnb cash on cash: 1.9% Traditional cash on cash: 2.96% Airbnb Rental Income: $3833 Traditional Rental Income: $3893 Airbnb ROI: 1.9% Traditional ROI: 2.96%
1815 SENECA BOULEVARD Winter Springs, FL This stunning 5-bedroom pool homeÂ in the highly desirable Chelsea Woods at TuscawillaÂ ha...	5 beds \| 5 baths \| 3,885 sq.ft.	$1,049,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $5397 Airbnb ROI: N/A Traditional ROI: 3.91%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Springs, FL

150 N EDGEMON AVENUE

Winter Springs, FL

3 beds | 1 baths | 1,008 sq.ft.

$289,999

Airbnb cash on cash: 2.44%

Traditional cash on cash: 6.7%

Airbnb Rental Income: $1827

Traditional Rental Income: $2498

Airbnb ROI: 2.44%

Traditional ROI: 6.7%

1029 ANTELOPE TRAIL

Winter Springs, FL

4 beds | 2 baths | 1,939 sq.ft.

$481,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $3833

Traditional Rental Income: $2835

Airbnb ROI: 4.66%

Traditional ROI: 4.29%

710 BRIARWOOD DRIVE

Winter Springs, FL

4 beds | 2 baths | 1,769 sq.ft.

$375,000

Airbnb cash on cash: 5.92%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $3833

Traditional Rental Income: $2724

Airbnb ROI: 5.92%

Traditional ROI: 5.12%

1331 AUGUSTA NATIONAL BOULEVARD

Winter Springs, FL

3 beds | 2 baths | 1,657 sq.ft.

$450,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1827

Traditional Rental Income: $2776

Airbnb ROI: 0.52%

Traditional ROI: 3.94%

337 KIRKCALDY DRIVE

Winter Springs, FL

2 beds | 2 baths | 974 sq.ft.

$287,900

Airbnb cash on cash: 2.52%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $1652

Traditional Rental Income: $1943

Airbnb ROI: 2.52%

Traditional ROI: 5.3%

131 LISA LOOP

Winter Springs, FL

4 beds | 3 baths | 2,309 sq.ft.

$489,000

Airbnb cash on cash: 4.04%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $3833

Traditional Rental Income: $3167

Airbnb ROI: 4.04%

Traditional ROI: 4.39%

1201 WOLVERINE TRAIL

Winter Springs, FL

4 beds | 2 baths | 1,979 sq.ft.

$500,000

Airbnb cash on cash: 4.09%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $3833

Traditional Rental Income: $2930

Airbnb ROI: 4.09%

Traditional ROI: 3.93%

1340 DELANEY DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,422 sq.ft.

$265,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 7.76%

Airbnb Rental Income: $1827

Traditional Rental Income: $2558

Airbnb ROI: 2.86%