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 69 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
150 N EDGEMON AVENUE Winter Springs, FL One or more photo(s) has been virtually staged. Welcome home to this 1959 Charming Home, t...	3 beds \| 1 baths \| 1,008 sq.ft.	$315,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 3.05% Airbnb Rental Income: $1827 Traditional Rental Income: $1594 Airbnb ROI: 2.17% Traditional ROI: 3.05%
1029 ANTELOPE TRAIL Winter Springs, FL Located in the highly desirable Tuscawilla community, this home offers an open floor plan ...	4 beds \| 2 baths \| 1,939 sq.ft.	$499,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 3.57% Airbnb Rental Income: $3833 Traditional Rental Income: $2587 Airbnb ROI: 4.46% Traditional ROI: 3.57%
1356 ORTEGA STREET Winter Springs, FL Welcome to this sweet Winter Springs home, perfectly suited for first-time buyers or growi...	3 beds \| 2 baths \| 1,036 sq.ft.	$398,500	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.33% Airbnb Rental Income: $1827 Traditional Rental Income: $1973 Airbnb ROI: 1.62% Traditional ROI: 3.33%
1163 SADDLEHORN CIRCLE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	3 beds \| 2 baths \| 1,462 sq.ft.	$425,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.92% Airbnb Rental Income: $1827 Traditional Rental Income: $2322 Airbnb ROI: 1.44% Traditional ROI: 3.92%
792 SENECA MEADOWS ROAD Winter Springs, FL Welcome to the highly sought after gated community of Parkstone in Winter Springs, an esta...	4 beds \| 3 baths \| 2,375 sq.ft.	$569,900	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.01% Airbnb Rental Income: $3833 Traditional Rental Income: $2819 Airbnb ROI: 3.36% Traditional ROI: 3.01%
1340 DELANEY DRIVE Winter Springs, FL Welcome to 1340 Delaney Drive, a move-in-ready home nestled in the heart of Winter Springs...	3 beds \| 2 baths \| 1,422 sq.ft.	$276,400	Airbnb cash on cash: 2.7% Traditional cash on cash: 6.19% Airbnb Rental Income: $1827 Traditional Rental Income: $2243 Airbnb ROI: 2.7% Traditional ROI: 6.19%
613 BONITA ROAD Winter Springs, FL Step into timeless charm and modern comfort at this custom-built Craftsman home in the hea...	4 beds \| 4 baths \| 3,281 sq.ft.	$765,000	Airbnb cash on cash: 2% Traditional cash on cash: 3.09% Airbnb Rental Income: $3833 Traditional Rental Income: $3785 Airbnb ROI: 2% Traditional ROI: 3.09%
1103 MARCUS COURT Winter Springs, FL This is how modern mid-century can be. Step into a beautiful blend of style, space, and co...	3 beds \| 3 baths \| 2,463 sq.ft.	$572,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.27% Airbnb Rental Income: $1827 Traditional Rental Income: $3095 Airbnb ROI: -0.03% Traditional ROI: 3.27%
838 DUNBAR TERRACE Winter Springs, FL This single-family residence is located in the established community of The Highlands in W...	3 beds \| 2 baths \| 1,313 sq.ft.	$399,999	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.85% Airbnb Rental Income: $1827 Traditional Rental Income: $2017 Airbnb ROI: 1.03% Traditional ROI: 2.85%
878 ELGIN DRIVE Winter Springs, FL Under contract-accepting backup offers. MOTIVATED SELLER/ AS IS CONTRACT- Step into comfor...	4 beds \| 3 baths \| 2,008 sq.ft.	$399,999	Airbnb cash on cash: 5.18% Traditional cash on cash: 4.25% Airbnb Rental Income: $3833 Traditional Rental Income: $2656 Airbnb ROI: 5.18% Traditional ROI: 4.25%
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.	$305,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.66% Airbnb Rental Income: $1827 Traditional Rental Income: $1873 Airbnb ROI: 1.79% Traditional ROI: 3.66%
112 REDTAIL PLACE Winter Springs, FL REDUCED $10,000! ! Luxurious Home in Eagles Watch - Gated Community Backing to Greenbelt! ...	3 beds \| 2 baths \| 2,000 sq.ft.	$519,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 2.53% Airbnb Rental Income: $1827 Traditional Rental Income: $2518 Airbnb ROI: 0.09% Traditional ROI: 2.53%
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%
31 S EDGEMON AVENUE Winter Springs, FL This charming home offers a spacious floor plan with a unique twistâ the garage has been...	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%
213 HEATHERWOOD COURT Winter Springs, FL Welcome to luxury living in the gated community of the Reserve at Tuscawilla! This elegant...	4 beds \| 4 baths \| 3,499 sq.ft.	$925,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 1.22% Airbnb Rental Income: $3833 Traditional Rental Income: $3336 Airbnb ROI: 0.84% Traditional ROI: 1.22%
746 N GRETNA COURT Winter Springs, FL Welcome to Your Dream Home in The Highlands of Winter Springs! This beautifully maintaine...	3 beds \| 2 baths \| 1,652 sq.ft.	$415,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 3.44% Airbnb Rental Income: $1827 Traditional Rental Income: $2358 Airbnb ROI: 0.81% Traditional ROI: 3.44%
1471 WESCOTT LOOP Winter Springs, FL Welcome to this expansive five bedroom, three bathroom retreat tucked inside a desirable g...	5 beds \| 3 baths \| 3,385 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.64% Airbnb Rental Income: $null Traditional Rental Income: $3023 Airbnb ROI: N/A Traditional ROI: 1.64%
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: 3.16% Airbnb Rental Income: $1827 Traditional Rental Income: $2672 Airbnb ROI: 0.29% Traditional ROI: 3.16%
45 S EDGEMON AVENUE Winter Springs, FL LOCATION LOCATION LOCATION This charming fully renovated home offers 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,387 sq.ft.	$365,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 4.81% Airbnb Rental Income: $1827 Traditional Rental Income: $2372 Airbnb ROI: 1.78% Traditional ROI: 4.81%
811 GATEHOUSE DRIVE Winter Springs, FL 2025 Roof Installed! A rare gem in a sought-after location, this stunning single-story ran...	3 beds \| 2 baths \| 2,022 sq.ft.	$489,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.88% Airbnb Rental Income: $1827 Traditional Rental Income: $2879 Airbnb ROI: 0.51% Traditional ROI: 3.88%
703 SAILFISH ROAD Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this charming, move-in-ready ho...	3 beds \| 2 baths \| 1,262 sq.ft.	$359,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.17% Airbnb Rental Income: $1827 Traditional Rental Income: $1948 Airbnb ROI: 1.35% Traditional ROI: 3.17%
294 SAN GABRIEL STREET Winter Springs, FL One or more photo(s) has been virtually staged. This 2-bedroom, 2-bath Winter Springs home...	2 beds \| 2 baths \| 1,105 sq.ft.	$245,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 4.34% Airbnb Rental Income: $1652 Traditional Rental Income: $1751 Airbnb ROI: 1.91% Traditional ROI: 4.34%
909 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL Welcome home! This charming Winter Springs property features high ceilings, an updated ki...	3 beds \| 2 baths \| 1,587 sq.ft.	$410,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.93% Airbnb Rental Income: $1827 Traditional Rental Income: $2282 Airbnb ROI: 1.46% Traditional ROI: 3.93%
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.	$785,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.29% Airbnb Rental Income: $3833 Traditional Rental Income: $3568 Airbnb ROI: 2.52% Traditional ROI: 3.29%
1121 ARBOR GLEN CIRCLE Winter Springs, FL WELCOME TO PARADISE! Unbeatable price for this stunning, move-in ready custom pool home in...	4 beds \| 3 baths \| 2,757 sq.ft.	$799,900	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.32% Airbnb Rental Income: $3833 Traditional Rental Income: $3715 Airbnb ROI: 2.37% Traditional ROI: 3.32%
1112 ORANGE AVENUE Winter Springs, FL This exquisite lakefront property in Orlando offers a unique blend of luxury and charm, se...	5 beds \| 7 baths \| 8,685 sq.ft.	$5,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.37% Airbnb Rental Income: $null Traditional Rental Income: $8770 Airbnb ROI: N/A Traditional ROI: 0.37%
821 SHALLOW BROOK AVENUE Winter Springs, FL STUNNING PRICE DROP ON THIS FABULOUS POOL HOME IN THE HEART OF WINTER SPRINGS! This stunn...	4 beds \| 3 baths \| 2,361 sq.ft.	$555,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 5.32% Airbnb Rental Income: $3833 Traditional Rental Income: $3703 Airbnb ROI: 3.97% Traditional ROI: 5.32%
625 Nighthawk Circle Winter Springs, FL This charming 3 bedroom, 2 bathroom single family home boasts a beautiful open plan. The k...	3 beds \| 2 baths \| 1,522 sq.ft.	$390,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.05% Airbnb Rental Income: $1827 Traditional Rental Income: $2105 Airbnb ROI: 1.94% Traditional ROI: 4.05%
1102 Winter Springs Boulevard Winter Springs, FL Fully remodeled home in the Tuskawilla Country Club neighborhood. This 3 bedroom 2 bathroo...	3 beds \| 2 baths \| 1,846 sq.ft.	$545,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.2% Airbnb Rental Income: $1827 Traditional Rental Income: $2259 Airbnb ROI: 0.38% Traditional ROI: 2.2%
704 FOREST VIEW COURT Winter Springs, FL MAJOR PRICE REDUCTION - EXCEPTIONAL OPPORTUNITY! Welcome to a masterpiece of modern design...	5 beds \| 3 baths \| 3,068 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $3852 Airbnb ROI: N/A Traditional ROI: 2.47%
909 DEVON CREEK ROAD Winter Springs, FL Welcome home to this stunning 4-bedroom, 3-bathroom residence located in the heart of Wint...	4 beds \| 3 baths \| 2,256 sq.ft.	$535,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 3.26% Airbnb Rental Income: $3833 Traditional Rental Income: $3018 Airbnb ROI: 3.23% Traditional ROI: 3.26%
227 Holiday Lane Winter Springs, FL Buyer contract fell through. No HOA - Updated Pool Home on Over Half an Acre with Privacy ...	3 beds \| 2 baths \| 1,708 sq.ft.	$479,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 3.56% Airbnb Rental Income: $1827 Traditional Rental Income: $2566 Airbnb ROI: 0.81% Traditional ROI: 3.56%
354 BRUSHWOOD LANE Winter Springs, FL Welcome to 354 Brushwood Lane in popular WINTER SPRINGS, FLORIDA! We proudly present this...	3 beds \| 2 baths \| 1,964 sq.ft.	$449,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 4.17% Airbnb Rental Income: $1827 Traditional Rental Income: $2777 Airbnb ROI: 0.74% Traditional ROI: 4.17%
930 ARABIAN AVENUE Winter Springs, FL Welcome to 930 Arabian Avenue, ideally located on what is widely regarded as the most beau...	4 beds \| 3 baths \| 4,105 sq.ft.	$1,050,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 2.56% Airbnb Rental Income: $3833 Traditional Rental Income: $3587 Airbnb ROI: 1.97% Traditional ROI: 2.56%
1352 ORTEGA STREET Winter Springs, FL Welcome to this beautifully updated, move-in ready, fully furnished 3-bedroom, 2-bath sing...	3 beds \| 2 baths \| 1,407 sq.ft.	$499,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.34% Airbnb Rental Income: $1827 Traditional Rental Income: $2299 Airbnb ROI: 1.27% Traditional ROI: 3.34%
409 Murphy rd Winter Springs, FL In the heart of Winter Springs lies your next model home or your next short-term cash-flow...	3 beds \| 2 baths \| N/A	$339,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 4.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2293 Airbnb ROI: 1.76% Traditional ROI: 4.76%
202 ARROWHEAD COURT Winter Springs, FL Unique, custom-built home on one half acre in the prestigious gated community of Arrowhead...	5 beds \| 5 baths \| 4,078 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $5979 Airbnb ROI: N/A Traditional ROI: 2.79%
951 GINNIE WAY Winter Springs, FL Move-in ready home and prime location! Welcome to Winter Springs Villageâwhere lifestyle...	3 beds \| 3 baths \| 1,794 sq.ft.	$459,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.92% Airbnb Rental Income: $1827 Traditional Rental Income: $2477 Airbnb ROI: 0.26% Traditional ROI: 2.92%
998 EL LAGO TERRACE Winter Springs, FL Seller may consider buyer concessions if made in an offer ~ Welcome to Sunrise Estates and...	4 beds \| 2 baths \| 2,126 sq.ft.	$625,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.63% Airbnb Rental Income: $3833 Traditional Rental Income: $2964 Airbnb ROI: 3.7% Traditional ROI: 3.63%
1001 KNOLL WOOD COURT Winter Springs, FL Searching for an IN-LAW SUITE? This is the home youâve been waiting for! Step inside thi...	4 beds \| 4 baths \| 1,855 sq.ft.	$455,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 5.3% Airbnb Rental Income: $3833 Traditional Rental Income: $3284 Airbnb ROI: 4.65% Traditional ROI: 5.3%

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.

$315,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $1827

Traditional Rental Income: $1594

Airbnb ROI: 2.17%

Traditional ROI: 3.05%

1029 ANTELOPE TRAIL

Winter Springs, FL

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

$499,000

Airbnb cash on cash: 4.46%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $3833

Traditional Rental Income: $2587

Airbnb ROI: 4.46%

Traditional ROI: 3.57%

1356 ORTEGA STREET

Winter Springs, FL

3 beds | 2 baths | 1,036 sq.ft.

$398,500

Airbnb cash on cash: 1.62%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $1827

Traditional Rental Income: $1973

Airbnb ROI: 1.62%

Traditional ROI: 3.33%

1163 SADDLEHORN CIRCLE

Winter Springs, FL

3 beds | 2 baths | 1,462 sq.ft.

$425,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $1827

Traditional Rental Income: $2322

Airbnb ROI: 1.44%

Traditional ROI: 3.92%

792 SENECA MEADOWS ROAD

Winter Springs, FL

4 beds | 3 baths | 2,375 sq.ft.

$569,900

Airbnb cash on cash: 3.36%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $3833

Traditional Rental Income: $2819

Airbnb ROI: 3.36%

Traditional ROI: 3.01%

1340 DELANEY DRIVE

Winter Springs, FL

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

$276,400

Airbnb cash on cash: 2.7%

Traditional cash on cash: 6.19%

Airbnb Rental Income: $1827

Traditional Rental Income: $2243

Airbnb ROI: 2.7%

Traditional ROI: 6.19%

613 BONITA ROAD

Winter Springs, FL

4 beds | 4 baths | 3,281 sq.ft.

$765,000

Airbnb cash on cash: 2%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $3833

Traditional Rental Income: $3785

Airbnb ROI: 2%

Traditional ROI: 3.09%

1103 MARCUS COURT

Winter Springs, FL

3 beds | 3 baths | 2,463 sq.ft.

$572,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1827

Traditional Rental Income: $3095

Airbnb ROI: -0.03%