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 74 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
1166 MAPIMI COURT Winter Springs, FL This move-in ready gem with a BRAND NEW AC SYSTEM (2025) is nestled on a quiet cul-de-sac ...	3 beds \| 2 baths \| 1,284 sq.ft.	$365,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.46% Airbnb Rental Income: $1827 Traditional Rental Income: $2015 Airbnb ROI: 1.47% Traditional ROI: 3.46%
213 ALMADEN COURT Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this delightful home, where com...	3 beds \| 2 baths \| 1,504 sq.ft.	$419,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.95% Airbnb Rental Income: $1827 Traditional Rental Income: $2372 Airbnb ROI: 1.32% Traditional ROI: 3.95%
1163 SADDLEHORN CIRCLE Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this stunning three-bedroom, tw...	3 beds \| 2 baths \| 1,462 sq.ft.	$437,860	Airbnb cash on cash: 1.37% Traditional cash on cash: 3.78% Airbnb Rental Income: $1827 Traditional Rental Income: $2322 Airbnb ROI: 1.37% Traditional ROI: 3.78%
116 VIEW POINT PLACE Winter Springs, FL SELLER IS OFFERING A $2,500 CREDIT TO BUYER WITH A FULL PRICED CONTRACT. Sitting on jus...	4 beds \| 3 baths \| 2,559 sq.ft.	$700,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 3.36% Airbnb Rental Income: $3833 Traditional Rental Income: $3534 Airbnb ROI: 2.55% Traditional ROI: 3.36%
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.	$580,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 2.94% Airbnb Rental Income: $3833 Traditional Rental Income: $2819 Airbnb ROI: 3.28% Traditional ROI: 2.94%
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.	$279,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 6.11% Airbnb Rental Income: $1827 Traditional Rental Income: $2243 Airbnb ROI: 2.66% Traditional ROI: 6.11%
707 CONESUS LANE Winter Springs, FL Welcome to this stunning 4-bedroom, 3-bath ranch-style pool home in the highly desirable T...	4 beds \| 3 baths \| 2,732 sq.ft.	$850,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.51% Airbnb Rental Income: $3833 Traditional Rental Income: $3683 Airbnb ROI: 1.66% Traditional ROI: 2.51%
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.	$309,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 3.6% Airbnb Rental Income: $1827 Traditional Rental Income: $1873 Airbnb ROI: 1.75% Traditional ROI: 3.6%
112 REDTAIL PLACE Winter Springs, FL Luxurious Home in Eagles Watch - Gated Community Backing to Greenbelt! Discover the perfec...	3 beds \| 2 baths \| 2,000 sq.ft.	$529,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.46% Airbnb Rental Income: $1827 Traditional Rental Income: $2518 Airbnb ROI: 0.07% Traditional ROI: 2.46%
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%
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.	$975,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 1.11% Airbnb Rental Income: $3833 Traditional Rental Income: $3336 Airbnb ROI: 0.75% Traditional ROI: 1.11%
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%
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%
1178 BLACK WALNUT COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. St...	4 beds \| 3 baths \| 2,841 sq.ft.	$625,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.82% Airbnb Rental Income: $3833 Traditional Rental Income: $3394 Airbnb ROI: 3.15% Traditional ROI: 3.82%
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.	$494,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.84% Airbnb Rental Income: $1827 Traditional Rental Income: $2879 Airbnb ROI: 0.5% Traditional ROI: 3.84%
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.	$374,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 3% Airbnb Rental Income: $1827 Traditional Rental Income: $1948 Airbnb ROI: 1.26% Traditional ROI: 3%
294 SAN GABRIEL STREET Winter Springs, FL One or more photo(s) has been virtually staged. Charming 2-bedroom, 2-bath, Move-In-Ready ...	2 beds \| 2 baths \| 1,105 sq.ft.	$260,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.04% Airbnb Rental Income: $1652 Traditional Rental Income: $1751 Airbnb ROI: 1.75% Traditional ROI: 4.04%
835 DYSON DRIVE Winter Springs, FL Under contract-accepting backup offers. Nestled on a sprawling 2.24-acre lot with NO HOA i...	4 beds \| 4 baths \| 3,595 sq.ft.	$1,020,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.92% Airbnb Rental Income: $3833 Traditional Rental Income: $5370 Airbnb ROI: 1.43% Traditional ROI: 3.92%
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.	$819,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.22% Airbnb Rental Income: $3833 Traditional Rental Income: $3715 Airbnb ROI: 2.29% Traditional ROI: 3.22%
912 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL The lowest priced single Family 3 bedroom home in Tuscawilla! Welcome to your peaceful ret...	3 beds \| 2 baths \| 1,795 sq.ft.	$379,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 4.52% Airbnb Rental Income: $1827 Traditional Rental Income: $2398 Airbnb ROI: 1.54% Traditional ROI: 4.52%
309 PANAMA CIRCLE Winter Springs, FL Outstanding Renovations! 3 BD 2 BT Home! New Update Kitchen with Quartz countertops. Stain...	3 beds \| 2 baths \| 1,482 sq.ft.	$356,500	Airbnb cash on cash: 2.4% Traditional cash on cash: 4.81% Airbnb Rental Income: $1827 Traditional Rental Income: $2141 Airbnb ROI: 2.4% Traditional ROI: 4.81%
315 PANAMA CIRCLE Winter Springs, FL Under contract-accepting backup offers. Discover modern living at 315 Panama Circle in bea...	4 beds \| 2 baths \| 1,206 sq.ft.	$335,000	Airbnb cash on cash: 8.05% Traditional cash on cash: 3.65% Airbnb Rental Income: $3833 Traditional Rental Income: $1622 Airbnb ROI: 8.05% Traditional ROI: 3.65%
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 NEW REDUCED PRICE! GREAT VALUE! COME SEE! If youâve just been waiting for the perfec...	4 beds \| 3 baths \| 2,361 sq.ft.	$587,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 4.98% Airbnb Rental Income: $3833 Traditional Rental Income: $3703 Airbnb ROI: 3.71% Traditional ROI: 4.98%
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%
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.	$789,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.43% Airbnb Rental Income: $null Traditional Rental Income: $4100 Airbnb ROI: N/A Traditional ROI: 3.43%
604 TIMBERWILDE COURT Winter Springs, FL Outstanding Grand 5 BD/3 Full Baths with a Large Bonus room can be a 6th bedroom, a fantas...	5 beds \| 3 baths \| 2,899 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $3767 Airbnb ROI: N/A Traditional ROI: 4.72%
1346 PALO ALTO COURT Winter Springs, FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 1,445 sq.ft.	$395,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.44% Airbnb Rental Income: $1827 Traditional Rental Income: $2157 Airbnb ROI: 1.22% Traditional ROI: 3.44%
422 S HAWTHORN CIRCLE Winter Springs, FL Under contract-accepting backup offers. This beautifully renovated 3 bedroom, 2 bath POOL ...	3 beds \| 2 baths \| 1,334 sq.ft.	$389,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 4.69% Airbnb Rental Income: $1827 Traditional Rental Income: $2539 Airbnb ROI: 1.39% Traditional ROI: 4.69%
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.	$549,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.17% Airbnb Rental Income: $1827 Traditional Rental Income: $2259 Airbnb ROI: 0.37% Traditional ROI: 2.17%
643 BLENHEIM LOOP Winter Springs, FL Under contract-accepting backup offers. Price Adjustment! FREE HOA until Jan 2026!! Step i...	4 beds \| 2 baths \| 1,947 sq.ft.	$475,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 4% Airbnb Rental Income: $3833 Traditional Rental Income: $2937 Airbnb ROI: 4.16% Traditional ROI: 4%
480 BUCKHORN DRIVE Winter Springs, FL Under contract-accepting backup offers. You donât want to miss this stunning 4-bedroom, ...	4 beds \| 4 baths \| 3,094 sq.ft.	$700,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 4.13% Airbnb Rental Income: $3833 Traditional Rental Income: $3995 Airbnb ROI: 2.61% Traditional ROI: 4.13%
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.	$549,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.14% Airbnb Rental Income: $3833 Traditional Rental Income: $3018 Airbnb ROI: 3.12% Traditional ROI: 3.14%
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.	$499,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 3.38% Airbnb Rental Income: $1827 Traditional Rental Income: $2566 Airbnb ROI: 0.74% Traditional ROI: 3.38%
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.	$495,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 3.7% Airbnb Rental Income: $1827 Traditional Rental Income: $2777 Airbnb ROI: 0.58% Traditional ROI: 3.7%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Springs, FL

1166 MAPIMI COURT

Winter Springs, FL

3 beds | 2 baths | 1,284 sq.ft.

$365,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1827

Traditional Rental Income: $2015

Airbnb ROI: 1.47%

Traditional ROI: 3.46%

213 ALMADEN COURT

Winter Springs, FL

3 beds | 2 baths | 1,504 sq.ft.

$419,900

Airbnb cash on cash: 1.32%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1827

Traditional Rental Income: $2372

Airbnb ROI: 1.32%

Traditional ROI: 3.95%

1163 SADDLEHORN CIRCLE

Winter Springs, FL

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

$437,860

Airbnb cash on cash: 1.37%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $1827

Traditional Rental Income: $2322

Airbnb ROI: 1.37%

Traditional ROI: 3.78%

116 VIEW POINT PLACE

Winter Springs, FL

4 beds | 3 baths | 2,559 sq.ft.

$700,000

Airbnb cash on cash: 2.55%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $3833

Traditional Rental Income: $3534

Airbnb ROI: 2.55%

Traditional ROI: 3.36%

792 SENECA MEADOWS ROAD

Winter Springs, FL

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

$580,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $3833

Traditional Rental Income: $2819

Airbnb ROI: 3.28%

Traditional ROI: 2.94%

1340 DELANEY DRIVE

Winter Springs, FL

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

$279,900

Airbnb cash on cash: 2.66%

Traditional cash on cash: 6.11%

Airbnb Rental Income: $1827

Traditional Rental Income: $2243

Airbnb ROI: 2.66%

Traditional ROI: 6.11%

707 CONESUS LANE

Winter Springs, FL

4 beds | 3 baths | 2,732 sq.ft.

$850,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $3833

Traditional Rental Income: $3683

Airbnb ROI: 1.66%

Traditional ROI: 2.51%

878 ELGIN DRIVE

Winter Springs, FL

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%