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.

Investment Property for Sale in Winter Springs, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
90 MOREE LOOP #15 Winter Springs, FL Welcome home to this beautifully updated 3-bedroom, 2- bath condo in the heart of Seminole...	3 beds \| 2 baths \| 1,187 sq.ft.	$199,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 6.44% Airbnb Rental Income: $1827 Traditional Rental Income: $1739 Airbnb ROI: 4.31% Traditional ROI: 6.44%
80 MOREE LOOP #10 Winter Springs, FL Welcome to The Highlands, a highly sought-after community in Winter Springs! This inviting...	3 beds \| 2 baths \| 1,187 sq.ft.	$159,999	Airbnb cash on cash: 5.58% Traditional cash on cash: 8.83% Airbnb Rental Income: $1827 Traditional Rental Income: $1830 Airbnb ROI: 5.58% Traditional ROI: 8.83%
466 CLUB DR Winter Springs, FL Under contract-accepting backup offers. Beautiful Single-Level Townhome in Winter Springs!...	3 beds \| 2 baths \| 1,182 sq.ft.	$282,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.04% Airbnb Rental Income: $1827 Traditional Rental Income: $2075 Airbnb ROI: 1.25% Traditional ROI: 4.04%
4522 BROOK HOLLOW CIRCLE Winter Springs, FL Seller will credit the buyer $5,000 towards the special assessment or closing costs! W...	2 beds \| 2 baths \| 1,108 sq.ft.	$270,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.17% Airbnb Rental Income: $1652 Traditional Rental Income: $1701 Airbnb ROI: 1.15% Traditional ROI: 3.17%
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%
451 HARBOR WINDS COURT Winter Springs, FL Well maintained! Move-in Ready! Fabulous 2-story, 3 bedroom, 2 full bath and a half bath t...	3 beds \| 3 baths \| 1,914 sq.ft.	$374,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.99% Airbnb Rental Income: $1827 Traditional Rental Income: $2496 Airbnb ROI: 0.68% Traditional ROI: 3.99%
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.	$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.	$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%
1432 WINTER WHARF LANE Winter Springs, FL One or more photo(s) has been virtually staged. ***This house comes with aÂ REDUCEDÂ RATEÂ...	3 beds \| 4 baths \| 2,184 sq.ft.	$400,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.09% Airbnb Rental Income: $1827 Traditional Rental Income: $3148 Airbnb ROI: 0.25% Traditional ROI: 5.09%
326 SAN MIGUEL STREET Winter Springs, FL Your Florida Lifestyle Awaits! Don't miss this completely and thoughtfully remodeled 3-bed...	3 beds \| 2 baths \| 1,032 sq.ft.	$234,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 4.89% Airbnb Rental Income: $1827 Traditional Rental Income: $1653 Airbnb ROI: 3.45% Traditional ROI: 4.89%
701 CASTLEWOOD DRIVE Winter Springs, FL Welcome to 701 Castlewood in the heart of Winter Springs, Florida! This inviting 3-bedroom...	3 beds \| 2 baths \| 1,470 sq.ft.	$295,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 4.71% Airbnb Rental Income: $1827 Traditional Rental Income: $2045 Airbnb ROI: 2.15% Traditional ROI: 4.71%
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%
602 CASA PARK COURT F Winter Springs, FL Under contract-accepting backup offers. Welcome to Casa Park Villas, where comfort meets c...	2 beds \| 3 baths \| 1,156 sq.ft.	$254,999	Airbnb cash on cash: 1.96% Traditional cash on cash: 4.34% Airbnb Rental Income: $1652 Traditional Rental Income: $1760 Airbnb ROI: 1.96% Traditional ROI: 4.34%
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%
718 LAKESIDE DRIVE Winter Springs, FL SELLER may consider Buyer credit with strong /acceptable Price., Spacious, move in rea...	2 beds \| 2 baths \| 1,166 sq.ft.	$298,900	Airbnb cash on cash: 1.51% Traditional cash on cash: 3.77% Airbnb Rental Income: $1652 Traditional Rental Income: $1824 Airbnb ROI: 1.51% Traditional ROI: 3.77%
1354 MILL STREAM LANE Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to your beautiful new home in the ...	3 beds \| 4 baths \| 2,288 sq.ft.	$429,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 3.38% Airbnb Rental Income: $1827 Traditional Rental Income: $2593 Airbnb ROI: 0.25% Traditional ROI: 3.38%
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%
611 CASA PARK A COURT Winter Springs, FL Under contract-accepting backup offers. Welcome to this beautifully updated 2 Bed, 2.5 Bat...	2 beds \| 3 baths \| 1,156 sq.ft.	$234,990	Airbnb cash on cash: 1.59% Traditional cash on cash: 3.82% Airbnb Rental Income: $1652 Traditional Rental Income: $1684 Airbnb ROI: 1.59% Traditional ROI: 3.82%
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%
600 NORTHERN WAY #502 Winter Springs, FL Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offer...	3 beds \| 2 baths \| 1,425 sq.ft.	$284,900	Airbnb cash on cash: 1.8% Traditional cash on cash: 4.68% Airbnb Rental Income: $1827 Traditional Rental Income: $2106 Airbnb ROI: 1.8% Traditional ROI: 4.68%
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%
4052 FALLING LILLY COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	5 beds \| 4 baths \| 1,960 sq.ft.	$340,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $3068 Airbnb ROI: N/A Traditional ROI: 5.9%
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%
1565 CORKERY COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Se...	3 beds \| 3 baths \| 1,846 sq.ft.	$459,900	Airbnb cash on cash: -0.87% Traditional cash on cash: 1.85% Airbnb Rental Income: $1827 Traditional Rental Income: $2505 Airbnb ROI: -0.87% Traditional ROI: 1.85%
1561 CORKERY COURT Winter Springs, FL One or more photo(s) has been virtually staged. A great deal! Seriously, this is the lowes...	2 beds \| 3 baths \| 1,854 sq.ft.	$379,900	Airbnb cash on cash: -1.34% Traditional cash on cash: 2.5% Airbnb Rental Income: $1652 Traditional Rental Income: $2555 Airbnb ROI: -1.34% Traditional ROI: 2.5%
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.	$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%
702 GLASGOW COURT Winter Springs, FL Two fenced in spaces for your dog ! Master bedroom DOWNSTAIRS Updated Townhome in Sought...	4 beds \| 3 baths \| 1,878 sq.ft.	$322,494	Airbnb cash on cash: 6.04% Traditional cash on cash: 5% Airbnb Rental Income: $3833 Traditional Rental Income: $2691 Airbnb ROI: 6.04% Traditional ROI: 5%
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%

Real Estate investment in Winter-springs, FL

There are 113 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $415,450 and the average price per square foot is $213. In October 2025, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,375.

Winter-springs, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 113 investment properties available for sale in Winter-springs.

In 2025, the best neighborhood to buy investment property is Winter Springs.

The ROI for Long-Term is higher than the Short-Term in Winter-springs with average rental income of $2,375.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Springs, FL

90 MOREE LOOP #15

Winter Springs, FL

3 beds | 2 baths | 1,187 sq.ft.

$199,900

Airbnb cash on cash: 4.31%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $1827

Traditional Rental Income: $1739

Airbnb ROI: 4.31%

Traditional ROI: 6.44%

80 MOREE LOOP #10

Winter Springs, FL

3 beds | 2 baths | 1,187 sq.ft.

$159,999

Airbnb cash on cash: 5.58%

Traditional cash on cash: 8.83%

Airbnb Rental Income: $1827

Traditional Rental Income: $1830

Airbnb ROI: 5.58%

Traditional ROI: 8.83%

466 CLUB DR

Winter Springs, FL

3 beds | 2 baths | 1,182 sq.ft.

$282,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1827

Traditional Rental Income: $2075

Airbnb ROI: 1.25%

Traditional ROI: 4.04%

4522 BROOK HOLLOW CIRCLE

Winter Springs, FL

2 beds | 2 baths | 1,108 sq.ft.

$270,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $1652

Traditional Rental Income: $1701

Airbnb ROI: 1.15%

Traditional ROI: 3.17%

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%

451 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,914 sq.ft.

$374,900

Airbnb cash on cash: 0.68%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $1827

Traditional Rental Income: $2496

Airbnb ROI: 0.68%

Traditional ROI: 3.99%

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%