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 Under contract-accepting backup offers. Welcome to The Highlands, a highly sought-after co...	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%
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%
150 N EDGEMON AVENUE Winter Springs, FL PRICE IMPROVEMENT AND SELLER MOTIVATED - $10,000 CREDIT TOWARDS BUYER'S RATE BUY-DOWN OR B...	3 beds \| 1 baths \| 1,008 sq.ft.	$314,500	Airbnb cash on cash: 2.18% Traditional cash on cash: 3.06% Airbnb Rental Income: $1827 Traditional Rental Income: $1594 Airbnb ROI: 2.18% Traditional ROI: 3.06%
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.	$495,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.6% Airbnb Rental Income: $3833 Traditional Rental Income: $2587 Airbnb ROI: 4.51% Traditional ROI: 3.6%
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.	$369,900	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.05% Airbnb Rental Income: $1827 Traditional Rental Income: $2496 Airbnb ROI: 0.71% Traditional ROI: 4.05%
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%
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.	$390,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 5.24% Airbnb Rental Income: $1827 Traditional Rental Income: $3148 Airbnb ROI: 0.28% Traditional ROI: 5.24%
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%
1355 CASA PARK CIRCLE Winter Springs, FL Casa Park Villas Townhome for Sale!! Great investment opportunity. Located in Tuscawilla...	2 beds \| 3 baths \| 1,156 sq.ft.	$245,900	Airbnb cash on cash: 1.39% Traditional cash on cash: 3.83% Airbnb Rental Income: $1652 Traditional Rental Income: $1754 Airbnb ROI: 1.39% Traditional ROI: 3.83%
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%
718 LAKESIDE DRIVE Winter Springs, FL Experience comfort and effortless living in this beautifully maintained Winter Springs hom...	2 beds \| 2 baths \| 1,166 sq.ft.	$289,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.93% Airbnb Rental Income: $1652 Traditional Rental Income: $1824 Airbnb ROI: 1.6% Traditional ROI: 3.93%
1230 SPOTTED SANDPIPER LOOP Winter Springs, FL Under contract-accepting backup offers. Welcome to this stunning tri-level townhouse featu...	4 beds \| 4 baths \| 2,359 sq.ft.	$499,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 3.82% Airbnb Rental Income: $3833 Traditional Rental Income: $3162 Airbnb ROI: 3.49% Traditional ROI: 3.82%
540 PINEBRANCH CIRCLE Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained tow...	3 beds \| 3 baths \| 1,602 sq.ft.	$350,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.06% Airbnb Rental Income: $1827 Traditional Rental Income: $2110 Airbnb ROI: 0.7% Traditional ROI: 3.06%
427 DIAMOND DOVE COVE Winter Springs, FL Spectacular Corner Townhome Awaits!!! Experience the lifestyle youâve always dreamed of...	4 beds \| 4 baths \| 2,344 sq.ft.	$496,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.49% Airbnb Rental Income: $3833 Traditional Rental Income: $3078 Airbnb ROI: 3.33% Traditional ROI: 3.49%
124 MCLEODS WAY Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. As...	2 beds \| 2 baths \| 1,129 sq.ft.	$325,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.35% Airbnb Rental Income: $1652 Traditional Rental Income: $1765 Airbnb ROI: 0.46% Traditional ROI: 2.35%
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%
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.	$425,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 3.42% Airbnb Rental Income: $1827 Traditional Rental Income: $2593 Airbnb ROI: 0.26% Traditional ROI: 3.42%
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%
113 MOCKINGBIRD LANE Winter Springs, FL Priced below Winter Springsâ average and ready for a quick sale, 113 Mockingbird Lane is...	4 beds \| 3 baths \| 2,207 sq.ft.	$483,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 4.09% Airbnb Rental Income: $3833 Traditional Rental Income: $2940 Airbnb ROI: 4.23% Traditional ROI: 4.09%
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%
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%
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%
1561 CORKERY COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. A ...	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.	$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%

Real Estate investment in Winter-springs, FL

There are 96 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $457,450 and the average price per square foot is $220. In December 2025, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,513.

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

There are 96 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 $2,513.

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%

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%

150 N EDGEMON AVENUE

Winter Springs, FL

3 beds | 1 baths | 1,008 sq.ft.

$314,500

Airbnb cash on cash: 2.18%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $1827

Traditional Rental Income: $1594

Airbnb ROI: 2.18%

Traditional ROI: 3.06%

1029 ANTELOPE TRAIL

Winter Springs, FL

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

$495,000

Airbnb cash on cash: 4.51%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $3833

Traditional Rental Income: $2587

Airbnb ROI: 4.51%

Traditional ROI: 3.6%

451 HARBOR WINDS COURT

Winter Springs, FL

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

$369,900

Airbnb cash on cash: 0.71%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $1827

Traditional Rental Income: $2496

Airbnb ROI: 0.71%

Traditional ROI: 4.05%

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%