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 82 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
710 BRIARWOOD DRIVE Winter Springs, FL Virtually Staged. MOVE-IN READY WITH NEW ROOF & HVAC SYSTEM TO BE COMPLETED PRIOR TO CLOSI...	4 beds \| 2 baths \| 1,769 sq.ft.	$360,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 5.37% Airbnb Rental Income: $3298 Traditional Rental Income: $2724 Airbnb ROI: 4.88% Traditional ROI: 5.37%
440 BUCKSKIN COURT Winter Springs, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 3 baths \| 1,922 sq.ft.	$525,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.37% Airbnb Rental Income: $3298 Traditional Rental Income: $2804 Airbnb ROI: 2.87% Traditional ROI: 3.37%
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: 3.07% Traditional cash on cash: 4.39% Airbnb Rental Income: $3298 Traditional Rental Income: $3167 Airbnb ROI: 3.07% 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: 3.14% Traditional cash on cash: 3.93% Airbnb Rental Income: $3298 Traditional Rental Income: $2930 Airbnb ROI: 3.14% Traditional ROI: 3.93%
1024 DINERO DRIVE Winter Springs, FL Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates ...	3 beds \| 2 baths \| 1,463 sq.ft.	$419,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.49% Airbnb Rental Income: $3583 Traditional Rental Income: $2341 Airbnb ROI: 4.65% Traditional ROI: 3.49%
613 BONITA ROAD Winter Springs, FL Under contract-accepting backup offers. Nestled beneath a canopy of mature trees in a char...	4 beds \| 4 baths \| 3,281 sq.ft.	$719,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.73% Airbnb Rental Income: $3298 Traditional Rental Income: $3368 Airbnb ROI: 1.52% Traditional ROI: 2.73%
4991 COURTLAND LOOP Winter Springs, FL Under contract-accepting backup offers. MULTIPLE OFFERS : HIGHEST AND BEST DUE BY SATURDAY...	4 beds \| 3 baths \| 3,217 sq.ft.	$750,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.02% Airbnb Rental Income: $3298 Traditional Rental Income: $3576 Airbnb ROI: 1.57% Traditional ROI: 3.02%
622 ANHINGA ROAD Winter Springs, FL $374,900 NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMAT...	3 beds \| 3 baths \| 1,721 sq.ft.	$374,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 5.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2709 Airbnb ROI: 5.27% Traditional ROI: 5.02%
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: 2.75% Traditional cash on cash: 2.23% Airbnb Rental Income: $3583 Traditional Rental Income: $2508 Airbnb ROI: 2.75% Traditional ROI: 2.23%
276 SAN GABRIEL STREET Winter Springs, FL Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportuni...	3 beds \| 2 baths \| 1,089 sq.ft.	$285,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 4.28% Airbnb Rental Income: $3583 Traditional Rental Income: $1998 Airbnb ROI: 7.25% Traditional ROI: 4.28%
130 SEVILLE CHASE DRIVE Winter Springs, FL Discover the perfect blend of comfort, privacy, and luxury in the sought-after gated commu...	4 beds \| 3 baths \| 2,433 sq.ft.	$739,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 1.86% Airbnb Rental Income: $3298 Traditional Rental Income: $2946 Airbnb ROI: 1.3% Traditional ROI: 1.86%
1551 WESCOTT LOOP Winter Springs, FL Welcome to Barrington Estates, where this light-filled home with an open floor plan instan...	4 beds \| 3 baths \| 2,803 sq.ft.	$750,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 2.36% Airbnb Rental Income: $3298 Traditional Rental Income: $3314 Airbnb ROI: 1.28% Traditional ROI: 2.36%
122 STONE GABLE CIR Winter Springs, FL Virtually Staged. PRICED TO SELL AT 469,900!! *** A 4 BEDROOM-FOOTPRINT IS ALREADY RECORDE...	3 beds \| 3 baths \| 2,147 sq.ft.	$469,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.37% Airbnb Rental Income: $3583 Traditional Rental Income: $3095 Airbnb ROI: 3.7% Traditional ROI: 4.37%
294 SAN GABRIEL STREET Winter Springs, FL Under contract-accepting backup offers. Beautifully maintained 2-bedroom, 2-bath single-fa...	2 beds \| 2 baths \| 1,105 sq.ft.	$249,990	Airbnb cash on cash: -0.83% Traditional cash on cash: 4% Airbnb Rental Income: $960 Traditional Rental Income: $1751 Airbnb ROI: -0.83% Traditional ROI: 4%
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.	$769,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.28% Airbnb Rental Income: $5023 Traditional Rental Income: $3908 Airbnb ROI: 3.4% Traditional ROI: 3.28%
998 EL LAGO TERRACE Winter Springs, FL PAID-OFF SOLAR! Welcome to Sunrise Estates and your opportunity to own a truly unique prop...	4 beds \| 2 baths \| 2,126 sq.ft.	$649,900	Airbnb cash on cash: 2.78% Traditional cash on cash: 4.08% Airbnb Rental Income: $3298 Traditional Rental Income: $3342 Airbnb ROI: 2.78% Traditional ROI: 4.08%
1360 VIA VILLA NOVA WAY Winter Springs, FL Location, Location, Location... Don't miss out this opportunity to own a turn-key home in ...	4 beds \| 2 baths \| 2,064 sq.ft.	$539,999	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.09% Airbnb Rental Income: $3298 Traditional Rental Income: $2955 Airbnb ROI: 3.3% Traditional ROI: 4.09%
934 TORREY PINE DRIVE Winter Springs, FL Virtually Staged. Beautifully remodeled golf course home in the highly desirable Tuscawill...	3 beds \| 2 baths \| 1,678 sq.ft.	$499,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.89% Airbnb Rental Income: $3583 Traditional Rental Income: $2726 Airbnb ROI: 4.04% Traditional ROI: 3.89%
314 SAN GABRIEL STREET Winter Springs, FL **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE ...	3 beds \| 2 baths \| 1,091 sq.ft.	$279,990	Airbnb cash on cash: 7.93% Traditional cash on cash: 5.5% Airbnb Rental Income: $3583 Traditional Rental Income: $2157 Airbnb ROI: 7.93% Traditional ROI: 5.5%
270 SAN GABRIEL STREET Winter Springs, FL Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springsânow offered...	3 beds \| 2 baths \| 1,089 sq.ft.	$249,900	Airbnb cash on cash: 9.75% Traditional cash on cash: 7.55% Airbnb Rental Income: $3583 Traditional Rental Income: $2278 Airbnb ROI: 9.75% Traditional ROI: 7.55%
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.	$305,500	Airbnb cash on cash: 5.8% Traditional cash on cash: 5.95% Airbnb Rental Income: $3298 Traditional Rental Income: $2602 Airbnb ROI: 5.8% Traditional ROI: 5.95%
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.	$725,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.97% Airbnb Rental Income: $5023 Traditional Rental Income: $4314 Airbnb ROI: 3.5% Traditional ROI: 3.97%
1815 SENECA BOULEVARD Winter Springs, FL Welcome to this beautifully reimagined 5-bedroom, 3 full bath, 2 half bath pool home locat...	5 beds \| 5 baths \| 3,885 sq.ft.	$998,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.16% Airbnb Rental Income: $5023 Traditional Rental Income: $5397 Airbnb ROI: 2.65% Traditional ROI: 4.16%
986 TURKEY HOLLOW CIRCLE Winter Springs, FL 986 Turkey Hollow Circleâwhere comfort, style, and Florida living come together beautifu...	4 beds \| 2 baths \| 1,864 sq.ft.	$494,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.94% Airbnb Rental Income: $3298 Traditional Rental Income: $3130 Airbnb ROI: 3.7% Traditional ROI: 4.94%
632 BLENHEIM LOOP Winter Springs, FL Good afternoon and welcome to your new 4 bedroom, 3 bathroom, and 2 car garage gated commu...	4 beds \| 3 baths \| 1,996 sq.ft.	$489,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 4.31% Airbnb Rental Income: $3298 Traditional Rental Income: $2946 Airbnb ROI: 3.47% Traditional ROI: 4.31%
101 PARTRIDGE CIRCLE Winter Springs, FL Under contract-accepting backup offers. Situated on a spacious 0.38-acre lot in the highly...	3 beds \| 2 baths \| 2,181 sq.ft.	$625,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 3.4% Airbnb Rental Income: $3583 Traditional Rental Income: $2907 Airbnb ROI: 3.22% Traditional ROI: 3.4%
30 SABLE COURT Winter Springs, FL REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community...	4 beds \| 3 baths \| 2,674 sq.ft.	$569,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 6% Airbnb Rental Income: $3298 Traditional Rental Income: $4099 Airbnb ROI: 3.11% Traditional ROI: 6%
214 CHESTNUT RIDGE STREET Winter Springs, FL Under contract-accepting backup offers. WOW, BEST PRICE IN Winter Springs! Executive TUSCA...	4 beds \| 3 baths \| 2,474 sq.ft.	$590,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.79% Airbnb Rental Income: $3298 Traditional Rental Income: $3292 Airbnb ROI: 2.46% Traditional ROI: 3.79%
421 HORIZON DRIVE Winter Springs, FL Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This mov...	3 beds \| 2 baths \| 1,069 sq.ft.	$294,900	Airbnb cash on cash: 6.93% Traditional cash on cash: 4.8% Airbnb Rental Income: $3583 Traditional Rental Income: $2205 Airbnb ROI: 6.93% Traditional ROI: 4.8%
1307 ORTEGA STREET Winter Springs, FL A home with its very own private oasis. This home boasts a 2019 AC UNIT and a 2021 ROOF RE...	3 beds \| 2 baths \| 1,881 sq.ft.	$430,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 4.61% Airbnb Rental Income: $3583 Traditional Rental Income: $2837 Airbnb ROI: 4.51% Traditional ROI: 4.61%
107 GOLDEN CREST COURT Winter Springs, FL Located within the gated community of Eagleâs Watch in Seminole County, this well-mainta...	3 beds \| 2 baths \| 1,978 sq.ft.	$504,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.21% Airbnb Rental Income: $3583 Traditional Rental Income: $2837 Airbnb ROI: 3.12% Traditional ROI: 3.21%
363 TWELVE OAKS DRIVE Winter Springs, FL Outstanding 5-bedroom, 3-bathroom home with a Screened Pool and a beautiful Water view. Ne...	5 beds \| 3 baths \| 3,408 sq.ft.	$537,000	Airbnb cash on cash: 5.76% Traditional cash on cash: 6.32% Airbnb Rental Income: $5023 Traditional Rental Income: $4276 Airbnb ROI: 5.76% Traditional ROI: 6.32%
130 DEER SONG DRIVE Winter Springs, FL Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to o...	3 beds \| 2 baths \| 1,105 sq.ft.	$310,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 5.17% Airbnb Rental Income: $3583 Traditional Rental Income: $2323 Airbnb ROI: 6.79% Traditional ROI: 5.17%
1825 SENECA BOULEVARD Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	4 beds \| 3 baths \| 2,711 sq.ft.	$650,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 4.7% Airbnb Rental Income: $3298 Traditional Rental Income: $3667 Airbnb ROI: 2.87% Traditional ROI: 4.7%
1113 CITRUS OAKS RUN Winter Springs, FL Under contract-accepting backup offers. Welcome to 1113 Citrus Oaks Run, a beautifully mai...	4 beds \| 3 baths \| 2,353 sq.ft.	$685,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 3.16% Airbnb Rental Income: $3298 Traditional Rental Income: $3253 Airbnb ROI: 2.08% Traditional ROI: 3.16%
448 MACGREGOR ROAD Winter Springs, FL Explore 448 MacGregor Rd, a individual residence with a straightforward design and integra...	2 beds \| 2 baths \| 1,477 sq.ft.	$350,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 4.71% Airbnb Rental Income: $960 Traditional Rental Income: $2084 Airbnb ROI: 0.23% Traditional ROI: 4.71%
702 GOLFPOINT DRIVE Winter Springs, FL Virtually Staged. SELLER MOTIVATED RARE OPPORTUNITY IN GLEN EAGLE/TUSCAWILLA! Set on a P...	5 beds \| 5 baths \| 3,660 sq.ft.	$899,900	Airbnb cash on cash: 2.32% Traditional cash on cash: 4.92% Airbnb Rental Income: $5023 Traditional Rental Income: $6175 Airbnb ROI: 2.32% Traditional ROI: 4.92%
120 N FAIRFAX AVENUE Winter Springs, FL Charming ranch-style home brimming with potential and ready for your personal touch! Ideal...	2 beds \| 1 baths \| 1,148 sq.ft.	$237,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.97% Airbnb Rental Income: $960 Traditional Rental Income: $1686 Airbnb ROI: 0.17% Traditional ROI: 4.97%
408 AVONDALE COURT Winter Springs, FL Under contract-accepting backup offers. Welcome to 408 Avondale Court, a custom estate bui...	5 beds \| 5 baths \| 3,850 sq.ft.	$1,250,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.5% Airbnb Rental Income: $5023 Traditional Rental Income: $6367 Airbnb ROI: 1.46% Traditional ROI: 3.5%
1702 DAVENPORT COURT Winter Springs, FL Under contract-accepting backup offers. Discover the perfect blend of comfort and convenie...	3 beds \| 2 baths \| 2,101 sq.ft.	$569,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 2.8% Airbnb Rental Income: $3583 Traditional Rental Income: $2838 Airbnb ROI: 2.73% Traditional ROI: 2.8%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Springs, FL

710 BRIARWOOD DRIVE

Winter Springs, FL

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

$360,000

Airbnb cash on cash: 4.88%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $3298

Traditional Rental Income: $2724

Airbnb ROI: 4.88%

Traditional ROI: 5.37%

440 BUCKSKIN COURT

Winter Springs, FL

4 beds | 3 baths | 1,922 sq.ft.

$525,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $3298

Traditional Rental Income: $2804

Airbnb ROI: 2.87%

Traditional ROI: 3.37%

131 LISA LOOP

Winter Springs, FL

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

$489,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $3298

Traditional Rental Income: $3167

Airbnb ROI: 3.07%

Traditional ROI: 4.39%

1201 WOLVERINE TRAIL

Winter Springs, FL

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

$500,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $3298

Traditional Rental Income: $2930

Airbnb ROI: 3.14%

Traditional ROI: 3.93%

1024 DINERO DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,463 sq.ft.

$419,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $3583

Traditional Rental Income: $2341

Airbnb ROI: 4.65%

Traditional ROI: 3.49%

613 BONITA ROAD

Winter Springs, FL

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

$719,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3298

Traditional Rental Income: $3368

Airbnb ROI: 1.52%

Traditional ROI: 2.73%

4991 COURTLAND LOOP

Winter Springs, FL

4 beds | 3 baths | 3,217 sq.ft.

$750,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $3298

Traditional Rental Income: $3576

Airbnb ROI: 1.57%

Traditional ROI: 3.02%

622 ANHINGA ROAD

Winter Springs, FL

3 beds | 3 baths | 1,721 sq.ft.

$374,900

Airbnb cash on cash: 5.27%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $3583

Traditional Rental Income: $2709

Airbnb ROI: 5.27%