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
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%
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%
466 CLUB DR Winter Springs, FL Beautiful Single-Level Townhome in Winter Springs! This charming single-level townhome se...	3 beds \| 2 baths \| 1,182 sq.ft.	$282,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.04% Airbnb Rental Income: $1827 Traditional Rental Income: $2075 Airbnb ROI: 1.25% Traditional ROI: 4.04%
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%
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%
1432 WINTER WHARF LANE Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to Jesups Landing, one of Winter S...	3 beds \| 4 baths \| 2,184 sq.ft.	$410,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 4.94% Airbnb Rental Income: $1827 Traditional Rental Income: $3148 Airbnb ROI: 0.22% Traditional ROI: 4.94%
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%
424 CLUB DRIVE Winter Springs, FL Welcome to this well-maintained 3-bedroom, 2-bath home located in the desirable Cypress Cl...	3 beds \| 2 baths \| 1,460 sq.ft.	$284,900	Airbnb cash on cash: 1.39% Traditional cash on cash: 3.98% Airbnb Rental Income: $1827 Traditional Rental Income: $2029 Airbnb ROI: 1.39% Traditional ROI: 3.98%
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%
479 HARBOR WINDS COURT Winter Springs, FL Beautiful Townhome in Gated Harbor Winds â Prime Location & Resort-Style Amenities! Donâ...	3 beds \| 3 baths \| 1,680 sq.ft.	$336,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.61% Airbnb Rental Income: $1827 Traditional Rental Income: $2188 Airbnb ROI: 0.91% Traditional ROI: 3.61%
701 CASTLEWOOD DRIVE Winter Springs, FL Welcome to 701 Castlewood, Winter Springs, Florida! This charming 3-bedroom, 2-bath home i...	3 beds \| 2 baths \| 1,470 sq.ft.	$299,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 4.64% Airbnb Rental Income: $1827 Traditional Rental Income: $2045 Airbnb ROI: 2.11% Traditional ROI: 4.64%
533 MOREE LOOP Winter Springs, FL Under contract-accepting backup offers. Tucked away in a peaceful, wooded setting, this 2-...	2 beds \| 3 baths \| 1,452 sq.ft.	$269,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.08% Airbnb Rental Income: $1652 Traditional Rental Income: $2016 Airbnb ROI: 0.83% Traditional ROI: 4.08%
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%
718 LAKESIDE DRIVE Winter Springs, FL Welcome to 718 LAKESIDE Drive in the heart of Winter Springs! This beautifully maintained ...	2 beds \| 2 baths \| 1,166 sq.ft.	$298,990	Airbnb cash on cash: 1.51% Traditional cash on cash: 3.77% Airbnb Rental Income: $1652 Traditional Rental Income: $1824 Airbnb ROI: 1.51% Traditional ROI: 3.77%
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%
1354 MILL STREAM LANE Winter Springs, FL Welcome to your beautiful new home in the heart of Winter Springs! This spacious and low-m...	3 beds \| 4 baths \| 2,288 sq.ft.	$429,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 3.38% Airbnb Rental Income: $1827 Traditional Rental Income: $2593 Airbnb ROI: 0.25% Traditional ROI: 3.38%
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%
611 CASA PARK A COURT Winter Springs, FL Welcome to this beautifully updated 2 Bed, 2.5 Bath townhome nestled in the desirable Casa...	2 beds \| 3 baths \| 1,156 sq.ft.	$245,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.63% Airbnb Rental Income: $1652 Traditional Rental Income: $1684 Airbnb ROI: 1.48% Traditional ROI: 3.63%
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%
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%
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%
452 Harbor Winds Court Winter Springs, FL Don't miss this beautifully maintained 3-bedroom, 2.5-bathroom townhome offering 1,914 sq ...	3 beds \| 3 baths \| 1,914 sq.ft.	$347,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 4.63% Airbnb Rental Income: $1827 Traditional Rental Income: $2293 Airbnb ROI: 1.68% Traditional ROI: 4.63%
4052 FALLING LILLY COURT Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this stunning 5-bedroom, 3.5-ba...	5 beds \| 4 baths \| 1,960 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.71% Airbnb Rental Income: $null Traditional Rental Income: $3068 Airbnb ROI: N/A Traditional ROI: 5.71%
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 One or more photo(s) has been virtually staged. Seller is extremely motivated and will giv...	3 beds \| 3 baths \| 1,846 sq.ft.	$475,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 1.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2505 Airbnb ROI: -0.87% Traditional ROI: 1.76%
1561 CORKERY COURT Winter Springs, FL One or more photo(s) has been virtually staged. A great deal! This immaculate townhome wit...	2 beds \| 3 baths \| 1,854 sq.ft.	$399,900	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.32% Airbnb Rental Income: $1652 Traditional Rental Income: $2555 Airbnb ROI: -1.32% Traditional ROI: 2.32%
554 PINEBRANCH CIRCLE Winter Springs, FL Short Sale. Short Sale - Move-In Ready Townhome in Exclusive Gated Barclay Reserve! Welcom...	2 beds \| 3 baths \| 1,558 sq.ft.	$320,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.48% Airbnb Rental Income: $1652 Traditional Rental Income: $2056 Airbnb ROI: 0.6% Traditional ROI: 3.48%
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%

Real Estate investment in Winter-springs, FL

There are 111 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $417,800 and the average price per square foot is $206. In September 2025, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,426.

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

There are 111 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 $2,426.

Your search for investment property begins and ends here

Investment Property 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%

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%

466 CLUB DR

Winter Springs, FL

3 beds | 2 baths | 1,182 sq.ft.

$282,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1827

Traditional Rental Income: $2075

Airbnb ROI: 1.25%

Traditional ROI: 4.04%

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%

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%

1432 WINTER WHARF LANE

Winter Springs, FL

3 beds | 4 baths | 2,184 sq.ft.

$410,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $1827

Traditional Rental Income: $3148

Airbnb ROI: 0.22%

Traditional ROI: 4.94%

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%