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 93 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 MOVE-IN READY WITH NEW ROOF & HVAC SYSTEM TO BE COMPLETED PRIOR TO CLOSING. Beautifully...	4 beds \| 2 baths \| 1,769 sq.ft.	$365,000	Airbnb cash on cash: 6.1% Traditional cash on cash: 5.28% Airbnb Rental Income: $3833 Traditional Rental Income: $2724 Airbnb ROI: 6.1% Traditional ROI: 5.28%
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.	$534,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.29% Airbnb Rental Income: $3833 Traditional Rental Income: $2804 Airbnb ROI: 3.7% Traditional ROI: 3.29%
1331 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL Under contract-accepting backup offers. 3 BED + OFFICE \| BRAND NEW ROOF \| WOODED LOT \| TUS...	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.	$284,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 5.37% Airbnb Rental Income: $1652 Traditional Rental Income: $1943 Airbnb ROI: 2.55% Traditional ROI: 5.37%
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: 4.04% Traditional cash on cash: 4.39% Airbnb Rental Income: $3833 Traditional Rental Income: $3167 Airbnb ROI: 4.04% Traditional ROI: 4.39%
758 N GRETNA COURT Winter Springs, FL Welcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both...	4 beds \| 3 baths \| 2,150 sq.ft.	$430,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 4.75% Airbnb Rental Income: $3833 Traditional Rental Income: $2892 Airbnb ROI: 5.04% Traditional ROI: 4.75%
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.	$424,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.44% Airbnb Rental Income: $1827 Traditional Rental Income: $2341 Airbnb ROI: 0.9% Traditional ROI: 3.44%
613 BONITA ROAD Winter Springs, FL Nestled beneath a canopy of mature trees in a charming ranch-style setting in Winter Sprin...	4 beds \| 4 baths \| 3,281 sq.ft.	$719,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 2.73% Airbnb Rental Income: $3833 Traditional Rental Income: $3368 Airbnb ROI: 2.19% 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: 2.21% Traditional cash on cash: 3.02% Airbnb Rental Income: $3833 Traditional Rental Income: $3576 Airbnb ROI: 2.21% Traditional ROI: 3.02%
622 ANHINGA ROAD Winter Springs, FL NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MIN...	3 beds \| 3 baths \| 1,721 sq.ft.	$384,900	Airbnb cash on cash: 1.06% Traditional cash on cash: 4.87% Airbnb Rental Income: $1827 Traditional Rental Income: $2709 Airbnb ROI: 1.06% Traditional ROI: 4.87%
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%
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.	$408,500	Airbnb cash on cash: 0.96% Traditional cash on cash: 5.01% Airbnb Rental Income: $1827 Traditional Rental Income: $2883 Airbnb ROI: 0.96% Traditional ROI: 5.01%
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: 1.8% Traditional cash on cash: 4.28% Airbnb Rental Income: $1827 Traditional Rental Income: $1998 Airbnb ROI: 1.8% 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: 1.95% Traditional cash on cash: 1.86% Airbnb Rental Income: $3833 Traditional Rental Income: $2946 Airbnb ROI: 1.95% Traditional ROI: 1.86%
201 BURGESS DRIVE Winter Springs, FL Welcome to Avery Park! This is a STUNNING 4-bedroom, 2.5-bath residence that spans more th...	4 beds \| 3 baths \| 3,046 sq.ft.	$650,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.43% Airbnb Rental Income: $3833 Traditional Rental Income: $3124 Airbnb ROI: 2.23% Traditional ROI: 2.43%
424 FLATWOOD DRIVE Winter Springs, FL Excellent opportunity in desirable Tusca Oaks/Tuscawilla area. Spacious 4BR/2.5BA with fun...	4 beds \| 4 baths \| 2,164 sq.ft.	$525,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 3.94% Airbnb Rental Income: $3833 Traditional Rental Income: $2889 Airbnb ROI: 4.17% Traditional ROI: 3.94%
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: 1.92% Traditional cash on cash: 2.36% Airbnb Rental Income: $3833 Traditional Rental Income: $3314 Airbnb ROI: 1.92% Traditional ROI: 2.36%
122 STONE GABLE CIR Winter Springs, FL PRICED TO SELL + $15,000 INCENTIVE!!. WELCOME TO YOUR COMPLETELY WORRY-FREE OASIS. SELLER ...	3 beds \| 3 baths \| 2,147 sq.ft.	$485,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 4.21% Airbnb Rental Income: $1827 Traditional Rental Income: $3095 Airbnb ROI: 0.33% Traditional ROI: 4.21%
294 SAN GABRIEL STREET Winter Springs, FL Beautifully maintained 2-bedroom, 2-bath single-family home located in the desirable Deers...	2 beds \| 2 baths \| 1,105 sq.ft.	$249,990	Airbnb cash on cash: 1.61% Traditional cash on cash: 4% Airbnb Rental Income: $1652 Traditional Rental Income: $1751 Airbnb ROI: 1.61% 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.	$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%
998 EL LAGO TERRACE Winter Springs, FL Welcome to Sunrise Estates and your opportunity to own a truly unique property in the hea...	4 beds \| 2 baths \| 2,126 sq.ft.	$650,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 4.07% Airbnb Rental Income: $3833 Traditional Rental Income: $3342 Airbnb ROI: 3.52% Traditional ROI: 4.07%
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: 4.19% Traditional cash on cash: 4.09% Airbnb Rental Income: $3833 Traditional Rental Income: $2955 Airbnb ROI: 4.19% Traditional ROI: 4.09%
934 TORREY PINE DRIVE Winter Springs, FL One or more photo(s) has been virtually staged. Beautifully remodeled golf course home in ...	3 beds \| 3 baths \| 1,678 sq.ft.	$514,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.75% Airbnb Rental Income: $1827 Traditional Rental Income: $2726 Airbnb ROI: 0.85% Traditional ROI: 3.75%
314 SAN GABRIEL STREET Winter Springs, FL Seller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome t...	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%
126 SEVILLE CHASE DRIVE Winter Springs, FL Price Improvement and a $20,000.00 SELLER CONCESSION towards buyer's closing costs ** ...	5 beds \| 4 baths \| 3,205 sq.ft.	$769,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.74% Airbnb Rental Income: $null Traditional Rental Income: $3844 Airbnb ROI: N/A Traditional ROI: 2.74%
270 SAN GABRIEL STREET Winter Springs, FL Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street...	3 beds \| 2 baths \| 1,089 sq.ft.	$259,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 7.26% Airbnb Rental Income: $1827 Traditional Rental Income: $2278 Airbnb ROI: 3.39% Traditional ROI: 7.26%
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: 7.35% Traditional cash on cash: 5.95% Airbnb Rental Income: $3833 Traditional Rental Income: $2602 Airbnb ROI: 7.35% 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.	$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%
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.	$999,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $5397 Airbnb ROI: N/A Traditional ROI: 4.15%
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.	$498,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 4.88% Airbnb Rental Income: $3833 Traditional Rental Income: $3130 Airbnb ROI: 4.61% Traditional ROI: 4.88%
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.	$495,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.26% Airbnb Rental Income: $3833 Traditional Rental Income: $2946 Airbnb ROI: 4.39% Traditional ROI: 4.26%
805 LEOPARD TRAIL Winter Springs, FL Under contract-accepting backup offers. Welcome to 805 Leopard Trail in Winter Springs, a ...	4 beds \| 2 baths \| 2,608 sq.ft.	$565,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 4.21% Airbnb Rental Income: $3833 Traditional Rental Income: $3144 Airbnb ROI: 3.95% Traditional ROI: 4.21%
903 TORREY PINE DRIVE Winter Springs, FL Under contract-accepting backup offers. NEW ROOF TO BE INSTALLED IN APRIL!! Paradise ...	3 beds \| 2 baths \| 1,501 sq.ft.	$469,900	Airbnb cash on cash: 1.05% Traditional cash on cash: 3.85% Airbnb Rental Income: $1827 Traditional Rental Income: $2566 Airbnb ROI: 1.05% Traditional ROI: 3.85%
120 E BAHAMA ROAD Winter Springs, FL Mid Century Modern Paradise!! A Beautiful, well-designed home with spectacular architectu...	4 beds \| 3 baths \| 4,464 sq.ft.	$1,249,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.69% Airbnb Rental Income: $3833 Traditional Rental Income: $4373 Airbnb ROI: 0.51% Traditional ROI: 1.69%
222 W PANAMA ROAD Winter Springs, FL POOL HOME + NEW ROOF! Welcome to this beautifully upgraded 3-bedroom, 2-bath residence wit...	3 beds \| 2 baths \| 1,044 sq.ft.	$310,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 5.75% Airbnb Rental Income: $1827 Traditional Rental Income: $2468 Airbnb ROI: 1.86% Traditional ROI: 5.75%
101 PARTRIDGE CIRCLE Winter Springs, FL Situated on a spacious 0.38-acre lot in the highly sought-after Tuscawilla community of Wi...	3 beds \| 2 baths \| 2,181 sq.ft.	$625,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.4% Airbnb Rental Income: $1827 Traditional Rental Income: $2907 Airbnb ROI: 0.71% 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: 3.95% Traditional cash on cash: 6% Airbnb Rental Income: $3833 Traditional Rental Income: $4099 Airbnb ROI: 3.95% Traditional ROI: 6%
214 CHESTNUT RIDGE STREET Winter Springs, FL WOW, BEST PRICE IN Winter Springs inside Executive TUSCAWILLA! Incredible opportunity. Her...	4 beds \| 3 baths \| 2,474 sq.ft.	$600,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 3.71% Airbnb Rental Income: $3833 Traditional Rental Income: $3292 Airbnb ROI: 3.2% Traditional ROI: 3.71%
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.	$299,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.7% Airbnb Rental Income: $1827 Traditional Rental Income: $2205 Airbnb ROI: 1.62% Traditional ROI: 4.7%
1219 SWAN STREET Winter Springs, FL Build your dream home on this rare 0.47 acre corner lot located at 1219 Swan Street in the...	3 beds \| 3 baths \| 1,848 sq.ft.	$350,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 5.87% Airbnb Rental Income: $1827 Traditional Rental Income: $2569 Airbnb ROI: 2.11% Traditional ROI: 5.87%

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.

$365,000

Airbnb cash on cash: 6.1%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $3833

Traditional Rental Income: $2724

Airbnb ROI: 6.1%

Traditional ROI: 5.28%

440 BUCKSKIN COURT

Winter Springs, FL

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

$534,900

Airbnb cash on cash: 3.7%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $3833

Traditional Rental Income: $2804

Airbnb ROI: 3.7%

Traditional ROI: 3.29%

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.

$284,900

Airbnb cash on cash: 2.55%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $1652

Traditional Rental Income: $1943

Airbnb ROI: 2.55%

Traditional ROI: 5.37%

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%

758 N GRETNA COURT

Winter Springs, FL

4 beds | 3 baths | 2,150 sq.ft.

$430,000

Airbnb cash on cash: 5.04%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $3833

Traditional Rental Income: $2892

Airbnb ROI: 5.04%

Traditional ROI: 4.75%

1024 DINERO DRIVE

Winter Springs, FL

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

$424,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1827

Traditional Rental Income: $2341

Airbnb ROI: 0.9%

Traditional ROI: 3.44%

613 BONITA ROAD

Winter Springs, FL

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

$719,000

Airbnb cash on cash: 2.19%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3833

Traditional Rental Income: $3368

Airbnb ROI: 2.19%