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.

Boro Investment Property for Sale in Winter Springs, FL

Search for Boro Investment Property for Sale in Winter Springs, Florida. Browse all of Mashvisor’s Boro Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 95 Boro Investment Property 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
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%
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.	$272,500	Airbnb cash on cash: 2.76% Traditional cash on cash: 6.3% Airbnb Rental Income: $1827 Traditional Rental Income: $2243 Airbnb ROI: 2.76% Traditional ROI: 6.3%
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.	$239,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.97% Airbnb Rental Income: $1652 Traditional Rental Income: $1754 Airbnb ROI: 1.46% Traditional ROI: 3.97%
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%
1427 WHITEHALL BOULEVARD Winter Springs, FL This GORGEOUS 3-bedroom SPLIT PLAN, 2 bath home is ready for its new owner's!! Beautiful ...	3 beds \| 2 baths \| 1,628 sq.ft.	$475,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.89% Airbnb Rental Income: $1827 Traditional Rental Income: $2347 Airbnb ROI: 0.61% Traditional ROI: 2.89%
1405 GOOLAGONG COURT Winter Springs, FL Welcome to this charming 2-bedroom, 2-bath home tucked inside the peaceful Wedgewood Tenni...	3 beds \| 2 baths \| 1,422 sq.ft.	$390,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.16% Airbnb Rental Income: $1827 Traditional Rental Income: $2120 Airbnb ROI: 1.01% Traditional ROI: 3.16%
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%
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%
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 Price improvement â excellent value in Winter Springs. This spacious 3BR/2BA home featur...	3 beds \| 2 baths \| 1,587 sq.ft.	$400,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 4.05% Airbnb Rental Income: $1827 Traditional Rental Income: $2282 Airbnb ROI: 1.53% Traditional ROI: 4.05%
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.	$769,900	Airbnb cash on cash: 2.5% Traditional cash on cash: 3.49% Airbnb Rental Income: $3833 Traditional Rental Income: $3715 Airbnb ROI: 2.5% Traditional ROI: 3.49%
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%

Your search for investment property begins and ends here

Boro 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%

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%

Traditional ROI: 3.92%

792 SENECA MEADOWS ROAD

Winter Springs, FL

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%