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 76 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
1009 TROON TRACE Winter Springs, FL Under contract-accepting backup offers. $25,000 PRICE REDUCTION. Priced for immediate sale...	4 beds \| 3 baths \| 1,681 sq.ft.	$390,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 3.64% Airbnb Rental Income: $3833 Traditional Rental Income: $2426 Airbnb ROI: 5.22% Traditional ROI: 3.64%
1166 MAPIMI COURT Winter Springs, FL This move-in ready gem is nestled on a quiet cul-de-sac with no rear neighbors and a vast ...	3 beds \| 2 baths \| 1,284 sq.ft.	$377,500	Airbnb cash on cash: 1.39% Traditional cash on cash: 3.32% Airbnb Rental Income: $1827 Traditional Rental Income: $2015 Airbnb ROI: 1.39% Traditional ROI: 3.32%
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.	$580,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 2.94% Airbnb Rental Income: $3833 Traditional Rental Income: $2819 Airbnb ROI: 3.28% Traditional ROI: 2.94%
977 TALON PLACE Winter Springs, FL Under contract-accepting backup offers. Welcome Home to Northern Oaks in Winter Springsâ...	4 beds \| 3 baths \| 2,712 sq.ft.	$650,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 2.46% Airbnb Rental Income: $3833 Traditional Rental Income: $3024 Airbnb ROI: 2.43% Traditional ROI: 2.46%
718 GLEN EAGLE DRIVE Winter Springs, FL Glen Eagle Elegant Custom Pool Home in Tuscawilla. Welcome to this beautiful home in the ...	4 beds \| 5 baths \| 3,004 sq.ft.	$839,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.26% Airbnb Rental Income: $3833 Traditional Rental Income: $4397 Airbnb ROI: 1.47% Traditional ROI: 3.26%
1126 SHADOWBROOK TRAIL Winter Springs, FL Donât miss out on this Beautiful 4 bedroom 3 bath Pool Home in the sought after Winding ...	4 beds \| 3 baths \| 2,368 sq.ft.	$609,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.86% Airbnb Rental Income: $3833 Traditional Rental Income: $3441 Airbnb ROI: 3.09% Traditional ROI: 3.86%
1155 OAK CREEK COURT Winter Springs, FL Peace, privacy, and timeless comfort await at this immaculate two-story home nestled on ov...	4 beds \| 3 baths \| 3,058 sq.ft.	$705,000	Airbnb cash on cash: 2.55% Traditional cash on cash: 3.72% Airbnb Rental Income: $3833 Traditional Rental Income: $3771 Airbnb ROI: 2.55% Traditional ROI: 3.72%
109 LIDO ROAD Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. NE...	3 beds \| 2 baths \| 1,150 sq.ft.	$364,999	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.48% Airbnb Rental Income: $1827 Traditional Rental Income: $2059 Airbnb ROI: 1.36% Traditional ROI: 3.48%
715 GLEN EAGLE DRIVE Winter Springs, FL Under contract-accepting backup offers. Elevate your lifestyle in this stunning, single-st...	4 beds \| 4 baths \| 2,800 sq.ft.	$825,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 3.44% Airbnb Rental Income: $3833 Traditional Rental Income: $4470 Airbnb ROI: 1.54% Traditional ROI: 3.44%
878 ELGIN DRIVE Winter Springs, FL Previous buyer felt on financing- MOTIVATED SELLER- Step into comfort and flexibility at 8...	4 beds \| 3 baths \| 2,008 sq.ft.	$440,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.78% Airbnb Rental Income: $3833 Traditional Rental Income: $2656 Airbnb ROI: 4.62% Traditional ROI: 3.78%
638 Coral Way Winter Springs, FL This beautiful 3 bed 2 bath home is a must see! NO HOA! The home sits on an oversized, fen...	3 beds \| 2 baths \| 1,554 sq.ft.	$464,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.22% Airbnb Rental Income: $1827 Traditional Rental Income: $2401 Airbnb ROI: 0.77% Traditional ROI: 3.22%
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%
944 TORREY PINE DRIVE Winter Springs, FL This light-filled home boasts beautiful views from the side of the home with a serene pond...	4 beds \| 3 baths \| 2,386 sq.ft.	$529,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 5.03% Airbnb Rental Income: $3833 Traditional Rental Income: $3942 Airbnb ROI: 3.13% Traditional ROI: 5.03%
31 S EDGEMON AVENUE Winter Springs, FL Charming Renovated Home in the Heart of Winter Springs Welcome to 31 S Edgemon Ave, a b...	3 beds \| 2 baths \| 1,270 sq.ft.	$352,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.92% Airbnb Rental Income: $1827 Traditional Rental Income: $2038 Airbnb ROI: 1.79% Traditional ROI: 3.92%
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%
1626 WOOD DUCK DRIVE Winter Springs, FL One or more photo(s) has been virtually staged. ***Welcome to your next opportunity in Tus...	4 beds \| 4 baths \| 4,335 sq.ft.	$975,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 2.37% Airbnb Rental Income: $3833 Traditional Rental Income: $4333 Airbnb ROI: 0.91% Traditional ROI: 2.37%
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.	$425,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.34% Airbnb Rental Income: $1827 Traditional Rental Income: $2358 Airbnb ROI: 0.77% Traditional ROI: 3.34%
965 TUSKAWILLA ROAD Winter Springs, FL Under contract-accepting backup offers. The price is right! Make the call to make this pro...	4 beds \| 3 baths \| 2,640 sq.ft.	$559,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 5.12% Airbnb Rental Income: $3833 Traditional Rental Income: $3446 Airbnb ROI: 4.28% Traditional ROI: 5.12%
540 SEVEN OAKS BOULEVARD Winter Springs, FL One or more photo(s) has been virtually staged. Step into a deluxe home designed to impres...	5 beds \| 4 baths \| 3,108 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $3752 Airbnb ROI: N/A Traditional ROI: 5.05%
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%
701 PALENCI COURT Winter Springs, FL **Equity opportunity for a savvy buyer. Please check the sold comps at 162 Seville Chase D...	4 beds \| 4 baths \| 3,489 sq.ft.	$688,800	Airbnb cash on cash: 2.43% Traditional cash on cash: 4.79% Airbnb Rental Income: $3833 Traditional Rental Income: $4520 Airbnb ROI: 2.43% Traditional ROI: 4.79%
811 GATEHOUSE DRIVE Winter Springs, FL A rare gem in a sought-after location, this stunning single-story ranch home sits on a nea...	3 beds \| 2 baths \| 2,022 sq.ft.	$495,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.83% Airbnb Rental Income: $1827 Traditional Rental Income: $2879 Airbnb ROI: 0.49% Traditional ROI: 3.83%
703 SAILFISH ROAD Winter Springs, FL Welcome to 703 Sailfish Rd in the desirable North Orlando Ranches subdivision of Winter Sp...	3 beds \| 2 baths \| 1,262 sq.ft.	$379,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 2.95% Airbnb Rental Income: $1827 Traditional Rental Income: $1948 Airbnb ROI: 1.23% Traditional ROI: 2.95%
294 SAN GABRIEL STREET Winter Springs, FL One or more photo(s) has been virtually staged. Move-In Ready & Full of Potential! This ch...	2 beds \| 2 baths \| 1,105 sq.ft.	$265,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.95% Airbnb Rental Income: $1652 Traditional Rental Income: $1751 Airbnb ROI: 1.69% Traditional ROI: 3.95%
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.	$819,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.22% Airbnb Rental Income: $3833 Traditional Rental Income: $3715 Airbnb ROI: 2.29% Traditional ROI: 3.22%
912 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL Under contract-accepting backup offers. The lowest priced single Family 3 bedroom home in ...	3 beds \| 2 baths \| 1,795 sq.ft.	$399,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.25% Airbnb Rental Income: $1827 Traditional Rental Income: $2398 Airbnb ROI: 1.41% Traditional ROI: 4.25%
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%
821 SHALLOW BROOK AVENUE Winter Springs, FL PRICE REDUCTION!!! If youâve just been waiting for the perfect house situated in the l...	4 beds \| 3 baths \| 2,361 sq.ft.	$597,700	Airbnb cash on cash: 3.63% Traditional cash on cash: 4.88% Airbnb Rental Income: $3833 Traditional Rental Income: $3703 Airbnb ROI: 3.63% Traditional ROI: 4.88%
625 Nighthawk Circle 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.	$404,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.83% Airbnb Rental Income: $1827 Traditional Rental Income: $2105 Airbnb ROI: 1.79% Traditional ROI: 3.83%
140 SEVILLE CHASE DRIVE Winter Springs, FL Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - a...	5 beds \| 4 baths \| 3,129 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $4100 Airbnb ROI: N/A Traditional ROI: 3.37%
309 KIRKCALDY DRIVE Winter Springs, FL Fully updated in 2025, including a BRAND NEW ROOF and NEW PLUMBING from a full re-pipe com...	3 beds \| 2 baths \| 1,326 sq.ft.	$300,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 4.54% Airbnb Rental Income: $1827 Traditional Rental Income: $2005 Airbnb ROI: 2.16% Traditional ROI: 4.54%
679 N ENDEAVOUR DR Winter Springs, FL Welcome to your dream home in the heart of Winter Springs! This beautifully updated four-b...	4 beds \| 3 baths \| 2,066 sq.ft.	$538,500	Airbnb cash on cash: 4.2% Traditional cash on cash: 5.81% Airbnb Rental Income: $3833 Traditional Rental Income: $3815 Airbnb ROI: 4.2% Traditional ROI: 5.81%
1542 WESCOTT LOOP Winter Springs, FL LARGE PRICE REDUCTION! Welcome Home to Barrington Estates Gated Community in the highl...	4 beds \| 3 baths \| 3,180 sq.ft.	$799,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 2.39% Airbnb Rental Income: $3833 Traditional Rental Income: $3231 Airbnb ROI: 2.09% Traditional ROI: 2.39%
435 BOXWOOD CIRCLE Winter Springs, FL Beautifully renovated 3-bedroom, 2-bath home in sought-after Winter Springsâaffordably p...	3 beds \| 2 baths \| 1,503 sq.ft.	$329,900	Airbnb cash on cash: 1.7% Traditional cash on cash: 4.46% Airbnb Rental Income: $1827 Traditional Rental Income: $2189 Airbnb ROI: 1.7% Traditional ROI: 4.46%
604 TIMBERWILDE COURT Winter Springs, FL Outstanding Grand 5 BD/3 Full Baths with a Large Bonus room can be a 6th bedroom, a fantas...	5 beds \| 3 baths \| 2,899 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $3767 Airbnb ROI: N/A Traditional ROI: 4.72%
1346 PALO ALTO COURT Winter Springs, FL Seller may consider buyer concessions if made in an offer ~ BACK ON MARKET! Welcome to Sun...	3 beds \| 2 baths \| 1,445 sq.ft.	$395,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.44% Airbnb Rental Income: $1827 Traditional Rental Income: $2157 Airbnb ROI: 1.22% Traditional ROI: 3.44%
1224 NORTHERN WAY Winter Springs, FL Home recently professionally appraised! This stunning 4-bedroom, 3.5-bath *custom-bui...	4 beds \| 4 baths \| 4,131 sq.ft.	$1,590,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 1.5% Airbnb Rental Income: $3833 Traditional Rental Income: $4585 Airbnb ROI: 0.43% Traditional ROI: 1.5%
995 TROON TRACE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. ON...	3 beds \| 3 baths \| 1,651 sq.ft.	$399,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.12% Airbnb Rental Income: $1827 Traditional Rental Income: $2279 Airbnb ROI: 0.6% Traditional ROI: 3.12%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Springs, FL

1009 TROON TRACE

Winter Springs, FL

4 beds | 3 baths | 1,681 sq.ft.

$390,000

Airbnb cash on cash: 5.22%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $3833

Traditional Rental Income: $2426

Airbnb ROI: 5.22%

Traditional ROI: 3.64%

1166 MAPIMI COURT

Winter Springs, FL

3 beds | 2 baths | 1,284 sq.ft.

$377,500

Airbnb cash on cash: 1.39%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1827

Traditional Rental Income: $2015

Airbnb ROI: 1.39%

Traditional ROI: 3.32%

792 SENECA MEADOWS ROAD

Winter Springs, FL

4 beds | 3 baths | 2,375 sq.ft.

$580,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $3833

Traditional Rental Income: $2819

Airbnb ROI: 3.28%

Traditional ROI: 2.94%

977 TALON PLACE

Winter Springs, FL

4 beds | 3 baths | 2,712 sq.ft.

$650,000

Airbnb cash on cash: 2.43%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $3833

Traditional Rental Income: $3024

Airbnb ROI: 2.43%

Traditional ROI: 2.46%

718 GLEN EAGLE DRIVE

Winter Springs, FL

4 beds | 5 baths | 3,004 sq.ft.

$839,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $3833

Traditional Rental Income: $4397

Airbnb ROI: 1.47%

Traditional ROI: 3.26%

1126 SHADOWBROOK TRAIL

Winter Springs, FL

4 beds | 3 baths | 2,368 sq.ft.

$609,000

Airbnb cash on cash: 3.09%

Traditional cash on cash: 3.86%

Airbnb Rental Income: $3833

Traditional Rental Income: $3441

Airbnb ROI: 3.09%

Traditional ROI: 3.86%

1155 OAK CREEK COURT

Winter Springs, FL

4 beds | 3 baths | 3,058 sq.ft.

$705,000

Airbnb cash on cash: 2.55%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $3833

Traditional Rental Income: $3771

Airbnb ROI: 2.55%

Traditional ROI: 3.72%

109 LIDO ROAD

Winter Springs, FL

3 beds | 2 baths | 1,150 sq.ft.

$364,999

Airbnb cash on cash: 1.36%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $1827

Traditional Rental Income: $2059

Airbnb ROI: 1.36%