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 115 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
1233 Stone Harbour Rd Winter Springs, FL Come home to soaring ceilings and designer finishes in this beautiful Winter Springs home....	5 beds \| 3 baths \| 2,908 sq.ft.	$739,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 0.62% Airbnb Rental Income: $3833 Traditional Rental Income: $1863 Airbnb ROI: 2.28% Traditional ROI: 0.62%
667 ANDOVER CIRCLE Winter Springs, FL Under contract-accepting backup offers. New Roof to be InstalledGeorgetowne of the Tus...	3 beds \| 2 baths \| 1,628 sq.ft.	$435,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.37% Airbnb Rental Income: $1827 Traditional Rental Income: $2322 Airbnb ROI: 0.95% Traditional ROI: 3.37%
150 N Edgemon Ave Winter Springs, FL One or more photo(s) has been virtually staged. FLASH SALE Motivated Seller!! Winter Spr...	3 beds \| 1 baths \| 1,008 sq.ft.	$289,999	Airbnb cash on cash: 2.44% Traditional cash on cash: 3.39% Airbnb Rental Income: $1827 Traditional Rental Income: $1594 Airbnb ROI: 2.44% Traditional ROI: 3.39%
1029 Antelope Trl 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.	$483,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.7% Airbnb Rental Income: $3833 Traditional Rental Income: $2587 Airbnb ROI: 4.62% Traditional ROI: 3.7%
1356 ORTEGA STREET Winter Springs, FL Under contract-accepting backup offers. New Roof at Closing. Pick your color! Perfectly su...	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%
1201 Wolverine Trl Winter Springs, FL Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighbo...	4 beds \| 2 baths \| 1,979 sq.ft.	$525,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 2.93% Airbnb Rental Income: $3833 Traditional Rental Income: $2554 Airbnb ROI: 3.85% Traditional ROI: 2.93%
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.	$265,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 6.5% Airbnb Rental Income: $1827 Traditional Rental Income: $2243 Airbnb ROI: 2.86% Traditional ROI: 6.5%
106 Thunberg Cv Winter Springs, FL Meticulously maintained and ideally located in the gated Howell Creek Reserve of Tuscawill...	4 beds \| 3 baths \| 2,501 sq.ft.	$690,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 2.77% Airbnb Rental Income: $3833 Traditional Rental Income: $3203 Airbnb ROI: 2.46% Traditional ROI: 2.77%
613 BONITA ROAD Winter Springs, FL Under contract-accepting backup offers. Step into timeless charm and modern comfort at thi...	4 beds \| 4 baths \| 3,281 sq.ft.	$749,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.18% Airbnb Rental Income: $3833 Traditional Rental Income: $3785 Airbnb ROI: 2.06% Traditional ROI: 3.18%
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 Under contract-accepting backup offers. MOTIVATED SELLERS, BRING AN OFFER!! This GORGEOUS ...	3 beds \| 2 baths \| 1,628 sq.ft.	$449,900	Airbnb cash on cash: 0.7% Traditional cash on cash: 3.11% Airbnb Rental Income: $1827 Traditional Rental Income: $2347 Airbnb ROI: 0.7% Traditional ROI: 3.11%
1405 GOOLAGONG COURT Winter Springs, FL Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 2-bath home tu...	2 beds \| 2 baths \| 1,422 sq.ft.	$375,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.32% Airbnb Rental Income: $1652 Traditional Rental Income: $2120 Airbnb ROI: 0.67% Traditional ROI: 3.32%
1163 BALTIC LANE Winter Springs, FL This lovingly maintained 4-bedroom, 2-bath home in a quiet neighborhood of sought-after Wi...	4 beds \| 2 baths \| 2,066 sq.ft.	$510,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.11% Airbnb Rental Income: $3833 Traditional Rental Income: $2630 Airbnb ROI: 3.9% Traditional ROI: 3.11%
622 Anhinga Rd Winter Springs, FL Price confirmed at $399,000 based on the completed 4-Point Inspection, which confirms the ...	3 beds \| 2 baths \| 1,721 sq.ft.	$394,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 3.72% Airbnb Rental Income: $1827 Traditional Rental Income: $2358 Airbnb ROI: 0.99% Traditional ROI: 3.72%
515 Seasons Ct 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%
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%
31 S Edgemon Ave 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 Ct 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%
1471 WESCOTT LOOP Winter Springs, FL Under contract-accepting backup offers. Welcome home to this expansive five-bedroom, three...	5 beds \| 3 baths \| 3,385 sq.ft.	$789,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.68% Airbnb Rental Income: $null Traditional Rental Income: $3023 Airbnb ROI: N/A Traditional ROI: 1.68%
122 Stone Gable Cir Winter Springs, FL ELEGANT CONTEMPORARY HOUSE WELCOMES YOU THROUGH A FOYER INTO THE LIVING/DINING AREA. THE H...	3 beds \| 2 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 Under contract-accepting backup offers. LOCATION LOCATION LOCATION This charming fully ren...	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.	$485,950	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.92% Airbnb Rental Income: $1827 Traditional Rental Income: $2879 Airbnb ROI: 0.52% Traditional ROI: 3.92%
1204 Swan St Winter Springs, FL Great location, No HOA..69 acres , 4 bedrooms,2 bathrooms, one half bathroom out door sho...	4 beds \| 2 baths \| 3,334 sq.ft.	$750,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 3.48% Airbnb Rental Income: $3833 Traditional Rental Income: $3568 Airbnb ROI: 2.68% Traditional ROI: 3.48%
1121 Arbor Glen Cir 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%
625 Nighthawk Cir 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.	$385,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.12% Airbnb Rental Income: $1827 Traditional Rental Income: $2105 Airbnb ROI: 1.98% Traditional ROI: 4.12%
1224 NORTHERN WAY Winter Springs, FL This stunning 4-bedroom, 3.5-bath custom-built* home offers luxury living on the **14t...	4 beds \| 4 baths \| 4,131 sq.ft.	$1,395,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 1.85% Airbnb Rental Income: $3833 Traditional Rental Income: $4585 Airbnb ROI: 0.63% Traditional ROI: 1.85%
1102 Winter Springs Blvd 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.	$535,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.25% Airbnb Rental Income: $1827 Traditional Rental Income: $2259 Airbnb ROI: 0.4% Traditional ROI: 2.25%
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 Under contract-accepting backup offers. Welcome home to this stunning 4-bedroom, 3-bathroo...	4 beds \| 3 baths \| 2,256 sq.ft.	$499,900	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.55% Airbnb Rental Income: $3833 Traditional Rental Income: $3018 Airbnb ROI: 3.53% Traditional ROI: 3.55%
930 Arabian Ave Winter Springs, FL Welcome to your dream home, a stunning estate style home on 1.2 acres of beautifully lands...	4 beds \| 2 baths \| 3,522 sq.ft.	$999,900	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%
206 CHARLES STREET Winter Springs, FL Do Not Miss OUT! Short Term Lease Option possible. Owner has invested over $35,000 in Rece...	4 beds \| 1 baths \| 1,120 sq.ft.	$285,000	Airbnb cash on cash: 8.68% Traditional cash on cash: 4.38% Airbnb Rental Income: $3833 Traditional Rental Income: $1851 Airbnb ROI: 8.68% Traditional ROI: 4.38%
1352 Ortega St Winter Springs, FL Welcome to this beautifully updated, move-in ready, fully furnished 3-bedroom, 2-bath sing...	3 beds \| 2 baths \| 1,407 sq.ft.	$470,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.6% Airbnb Rental Income: $1827 Traditional Rental Income: $2299 Airbnb ROI: 1.41% Traditional ROI: 3.6%
409 Murphy rd Winter Springs, FL In the heart of Winter Springs lies your next model home or your next short-term cash-flow...	3 beds \| 2 baths \| N/A	$339,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 4.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2293 Airbnb ROI: 1.76% Traditional ROI: 4.76%
202 Arrowhead Ct Winter Springs, FL Under contract-accepting backup offers. BRAND NEW TILE ROOF! Gorgeous custom-built home on...	5 beds \| 4 baths \| 4,078 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $5979 Airbnb ROI: N/A Traditional ROI: 2.79%
998 EL LAGO TERRACE Winter Springs, FL Seller may consider buyer concessions if made in an offer ~ Welcome to Sunrise Estates and...	4 beds \| 2 baths \| 2,126 sq.ft.	$700,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 3.14% Airbnb Rental Income: $3833 Traditional Rental Income: $2964 Airbnb ROI: 3.2% Traditional ROI: 3.14%
1399 BRAVE WOLF POINT Winter Springs, FL Under contract-accepting backup offers. Under Contract Accepting Back Up Offers! Available...	5 beds \| 3 baths \| 2,542 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.36% Airbnb Rental Income: $null Traditional Rental Income: $2899 Airbnb ROI: N/A Traditional ROI: 2.36%
1816 Seneca Blvd Winter Springs, FL Welcome to this beautifully maintained Tuscawilla home! This 5 bedroom, 4 bathroom, POOL h...	5 beds \| 4 baths \| 3,130 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $3758 Airbnb ROI: N/A Traditional ROI: 3.25%
934 Torrey Pine Dr Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to Greenbriar at Tuscawilla, where...	3 beds \| 2 baths \| 1,678 sq.ft.	$415,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.78% Airbnb Rental Income: $1827 Traditional Rental Income: $2305 Airbnb ROI: 1.28% Traditional ROI: 3.78%
314 San Gabriel St Winter Springs, FL Welcome home to this charming 3 bedroom, 2 Bath home in the heart of Winter Springs, in ce...	3 beds \| 2 baths \| 1,091 sq.ft.	$279,990	Airbnb cash on cash: 2.39% Traditional cash on cash: 4.46% Airbnb Rental Income: $1827 Traditional Rental Income: $1883 Airbnb ROI: 2.39% Traditional ROI: 4.46%
724 Indian Ct Winter Springs, FL This beautiful 4-bedroom, 3-bathroom home at 724 Indian Ct in Winter Springs offers 2,092 ...	4 beds \| 3 baths \| 2,092 sq.ft.	$450,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 5.18% Airbnb Rental Income: $3833 Traditional Rental Income: $3217 Airbnb ROI: 4.68% Traditional ROI: 5.18%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Springs, FL

1233 Stone Harbour Rd

Winter Springs, FL

5 beds | 3 baths | 2,908 sq.ft.

$739,900

Airbnb cash on cash: 2.28%

Traditional cash on cash: 0.62%

Airbnb Rental Income: $3833

Traditional Rental Income: $1863

Airbnb ROI: 2.28%

Traditional ROI: 0.62%

667 ANDOVER CIRCLE

Winter Springs, FL

3 beds | 2 baths | 1,628 sq.ft.

$435,000

Airbnb cash on cash: 0.95%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $1827

Traditional Rental Income: $2322

Airbnb ROI: 0.95%

Traditional ROI: 3.37%

150 N Edgemon Ave

Winter Springs, FL

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

$289,999

Airbnb cash on cash: 2.44%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $1827

Traditional Rental Income: $1594

Airbnb ROI: 2.44%

Traditional ROI: 3.39%

1029 Antelope Trl

Winter Springs, FL

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

$483,000

Airbnb cash on cash: 4.62%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $3833

Traditional Rental Income: $2587

Airbnb ROI: 4.62%

Traditional ROI: 3.7%

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%

1201 Wolverine Trl

Winter Springs, FL

4 beds | 2 baths | 1,979 sq.ft.

$525,000

Airbnb cash on cash: 3.85%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $3833

Traditional Rental Income: $2554

Airbnb ROI: 3.85%

Traditional ROI: 2.93%

1340 DELANEY DRIVE

Winter Springs, FL

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

$265,000

Airbnb cash on cash: 2.86%

Traditional cash on cash: 6.5%

Airbnb Rental Income: $1827

Traditional Rental Income: $2243

Airbnb ROI: 2.86%

Traditional ROI: 6.5%

106 Thunberg Cv

Winter Springs, FL

4 beds | 3 baths | 2,501 sq.ft.

$690,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $3833

Traditional Rental Income: $3203

Airbnb ROI: 2.46%