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.

Memphis Investment Property for Sale in Winter Springs, FL

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

Showing 114 Memphis 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 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%
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 Welcome to your next home! This delightful open and bright 3-bedroom, 1-bath residence off...	3 beds \| 1 baths \| 1,008 sq.ft.	$325,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 2.93% Airbnb Rental Income: $1827 Traditional Rental Income: $1594 Airbnb ROI: 2.08% Traditional ROI: 2.93%
1166 MAPIMI COURT Winter Springs, FL Under contract-accepting backup offers. This move-in ready gem with a BRAND NEW AC SYSTEM ...	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.	$430,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.87% Airbnb Rental Income: $1827 Traditional Rental Income: $2322 Airbnb ROI: 1.41% Traditional ROI: 3.87%
116 VIEW POINT PLACE Winter Springs, FL Under contract-accepting backup offers. Sitting on just under a Â½-acre lot, this 4-bedroo...	4 beds \| 3 baths \| 2,559 sq.ft.	$689,500	Airbnb cash on cash: 2.61% Traditional cash on cash: 3.43% Airbnb Rental Income: $3833 Traditional Rental Income: $3534 Airbnb ROI: 2.61% Traditional ROI: 3.43%
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.	$395,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 5.16% Airbnb Rental Income: $1827 Traditional Rental Income: $3148 Airbnb ROI: 0.26% Traditional ROI: 5.16%
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%
718 GLEN EAGLE DRIVE Winter Springs, FL Under contract-accepting backup offers. Glen Eagle Elegant Custom Pool Home in Tuscawilla....	4 beds \| 5 baths \| 3,004 sq.ft.	$770,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.63% Airbnb Rental Income: $3833 Traditional Rental Income: $4397 Airbnb ROI: 1.69% Traditional ROI: 3.63%
1155 OAK CREEK COURT Winter Springs, FL Under contract-accepting backup offers. 4/3 + Pvt Office with oversized 2 car garage. Plen...	4 beds \| 3 baths \| 3,058 sq.ft.	$675,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 3.93% Airbnb Rental Income: $3833 Traditional Rental Income: $3771 Airbnb ROI: 2.71% Traditional ROI: 3.93%
701 CASTLEWOOD DRIVE Winter Springs, FL Under contract-accepting backup offers. Welcome to 701 Castlewood in the heart of Winter S...	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.	$525,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.49% Airbnb Rental Income: $1827 Traditional Rental Income: $2518 Airbnb ROI: 0.08% Traditional ROI: 2.49%
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 Spacious, move in ready, with LOW HOA , Welcome to 718 LAKESIDE Drive in the heart of Wint...	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%
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%
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.	$950,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.16% Airbnb Rental Income: $3833 Traditional Rental Income: $3336 Airbnb ROI: 0.79% Traditional ROI: 1.16%
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 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.	$492,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.86% Airbnb Rental Income: $1827 Traditional Rental Income: $2879 Airbnb ROI: 0.5% Traditional ROI: 3.86%
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.	$369,900	Airbnb cash on cash: 1.29% Traditional cash on cash: 3.06% Airbnb Rental Income: $1827 Traditional Rental Income: $1948 Airbnb ROI: 1.29% Traditional ROI: 3.06%
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.	$255,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 4.14% Airbnb Rental Income: $1652 Traditional Rental Income: $1751 Airbnb ROI: 1.8% Traditional ROI: 4.14%
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.	$322,493	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%

Your search for investment property begins and ends here

Memphis 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.

$325,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $1827

Traditional Rental Income: $1594

Airbnb ROI: 2.08%

Traditional ROI: 2.93%

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.

$430,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $1827

Traditional Rental Income: $2322

Airbnb ROI: 1.41%