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
710 BRIARWOOD DRIVE Winter Springs, FL Virtually Staged. MOVE-IN READY WITH NEW ROOF & HVAC SYSTEM TO BE COMPLETED PRIOR TO CLOSI...	4 beds \| 2 baths \| 1,769 sq.ft.	$360,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 5.37% Airbnb Rental Income: $3298 Traditional Rental Income: $2724 Airbnb ROI: 4.88% Traditional ROI: 5.37%
440 BUCKSKIN COURT Winter Springs, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	4 beds \| 3 baths \| 1,922 sq.ft.	$525,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.37% Airbnb Rental Income: $3298 Traditional Rental Income: $2804 Airbnb ROI: 2.87% Traditional ROI: 3.37%
451 HARBOR WINDS COURT Winter Springs, FL Under contract-accepting backup offers. Virtually Staged. Welcome to 451 Harbor Winds Cour...	3 beds \| 3 baths \| 1,914 sq.ft.	$357,500	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.53% Airbnb Rental Income: $3583 Traditional Rental Income: $2637 Airbnb ROI: 5.01% Traditional ROI: 4.53%
471 HARBOR WINDS COURT Winter Springs, FL Welcome to your own slice of Winter Springs paradise at 417 Harbor Winds Court! Tucked awa...	3 beds \| 3 baths \| 1,680 sq.ft.	$330,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.74% Airbnb Rental Income: $3583 Traditional Rental Income: $2627 Airbnb ROI: 5.28% Traditional ROI: 4.74%
131 LISA LOOP Winter Springs, FL Check out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly ...	4 beds \| 3 baths \| 2,309 sq.ft.	$489,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 4.39% Airbnb Rental Income: $3298 Traditional Rental Income: $3167 Airbnb ROI: 3.07% Traditional ROI: 4.39%
1201 WOLVERINE TRAIL 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.	$500,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 3.93% Airbnb Rental Income: $3298 Traditional Rental Income: $2930 Airbnb ROI: 3.14% Traditional ROI: 3.93%
1024 DINERO DRIVE Winter Springs, FL Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates ...	3 beds \| 2 baths \| 1,463 sq.ft.	$419,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.49% Airbnb Rental Income: $3583 Traditional Rental Income: $2341 Airbnb ROI: 4.65% Traditional ROI: 3.49%
299 WOODGREEN LANE Winter Springs, FL Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Gre...	3 beds \| 3 baths \| 1,326 sq.ft.	$285,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 4.13% Airbnb Rental Income: $3583 Traditional Rental Income: $1876 Airbnb ROI: 7.56% Traditional ROI: 4.13%
499 CLUB DRIVE Winter Springs, FL Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices fo...	2 beds \| 2 baths \| 1,224 sq.ft.	$235,000	Airbnb cash on cash: -2.11% Traditional cash on cash: 4.57% Airbnb Rental Income: $960 Traditional Rental Income: $2096 Airbnb ROI: -2.11% Traditional ROI: 4.57%
412 BLUE BAYOU LANE Winter Springs, FL PRICED TO SELL - Quick move in available. Welcome to 412 Blue Bayou Lane in the highly des...	3 beds \| 4 baths \| 1,854 sq.ft.	$380,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 6.49% Airbnb Rental Income: $3583 Traditional Rental Income: $3430 Airbnb ROI: 4.71% Traditional ROI: 6.49%
613 BONITA ROAD Winter Springs, FL Under contract-accepting backup offers. Nestled beneath a canopy of mature trees in a char...	4 beds \| 4 baths \| 3,281 sq.ft.	$719,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.73% Airbnb Rental Income: $3298 Traditional Rental Income: $3368 Airbnb ROI: 1.52% Traditional ROI: 2.73%
4991 COURTLAND LOOP Winter Springs, FL Under contract-accepting backup offers. MULTIPLE OFFERS : HIGHEST AND BEST DUE BY SATURDAY...	4 beds \| 3 baths \| 3,217 sq.ft.	$750,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.02% Airbnb Rental Income: $3298 Traditional Rental Income: $3576 Airbnb ROI: 1.57% Traditional ROI: 3.02%
622 ANHINGA ROAD Winter Springs, FL $374,900 NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMAT...	3 beds \| 3 baths \| 1,721 sq.ft.	$374,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 5.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2709 Airbnb ROI: 5.27% Traditional ROI: 5.02%
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: 2.75% Traditional cash on cash: 2.23% Airbnb Rental Income: $3583 Traditional Rental Income: $2508 Airbnb ROI: 2.75% Traditional ROI: 2.23%
600 NORTHERN WAY #302 Winter Springs, FL Under contract-accepting backup offers. Virtually Staged. Seller may consider buyer conces...	3 beds \| 2 baths \| 1,425 sq.ft.	$269,900	Airbnb cash on cash: 5.41% Traditional cash on cash: 3.17% Airbnb Rental Income: $3583 Traditional Rental Income: $2226 Airbnb ROI: 5.41% Traditional ROI: 3.17%
276 SAN GABRIEL STREET Winter Springs, FL Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportuni...	3 beds \| 2 baths \| 1,089 sq.ft.	$285,000	Airbnb cash on cash: 7.25% Traditional cash on cash: 4.28% Airbnb Rental Income: $3583 Traditional Rental Income: $1998 Airbnb ROI: 7.25% Traditional ROI: 4.28%
130 SEVILLE CHASE DRIVE Winter Springs, FL Discover the perfect blend of comfort, privacy, and luxury in the sought-after gated commu...	4 beds \| 3 baths \| 2,433 sq.ft.	$739,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 1.86% Airbnb Rental Income: $3298 Traditional Rental Income: $2946 Airbnb ROI: 1.3% Traditional ROI: 1.86%
444 BLUE BAYOU LANE Winter Springs, FL Welcome to 444 Blue Bayou Lane, a fully renovated 3-story end-unit townhome in a prime loc...	3 beds \| 4 baths \| 1,854 sq.ft.	$385,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 2.78% Airbnb Rental Income: $3583 Traditional Rental Income: $2431 Airbnb ROI: 3.79% Traditional ROI: 2.78%
1551 WESCOTT LOOP Winter Springs, FL Welcome to Barrington Estates, where this light-filled home with an open floor plan instan...	4 beds \| 3 baths \| 2,803 sq.ft.	$750,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 2.36% Airbnb Rental Income: $3298 Traditional Rental Income: $3314 Airbnb ROI: 1.28% Traditional ROI: 2.36%
122 STONE GABLE CIR Winter Springs, FL Virtually Staged. PRICED TO SELL AT 469,900!! *** A 4 BEDROOM-FOOTPRINT IS ALREADY RECORDE...	3 beds \| 3 baths \| 2,147 sq.ft.	$469,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.37% Airbnb Rental Income: $3583 Traditional Rental Income: $3095 Airbnb ROI: 3.7% Traditional ROI: 4.37%
294 SAN GABRIEL STREET Winter Springs, FL Under contract-accepting backup offers. Beautifully maintained 2-bedroom, 2-bath single-fa...	2 beds \| 2 baths \| 1,105 sq.ft.	$249,990	Airbnb cash on cash: -0.83% Traditional cash on cash: 4% Airbnb Rental Income: $960 Traditional Rental Income: $1751 Airbnb ROI: -0.83% Traditional ROI: 4%
702 GLASGOW COURT Winter Springs, FL Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac ...	4 beds \| 3 baths \| 1,878 sq.ft.	$313,700	Airbnb cash on cash: 4.63% Traditional cash on cash: 5.07% Airbnb Rental Income: $3298 Traditional Rental Income: $2691 Airbnb ROI: 4.63% Traditional ROI: 5.07%
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.	$769,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.28% Airbnb Rental Income: $5023 Traditional Rental Income: $3908 Airbnb ROI: 3.4% Traditional ROI: 3.28%
30 MOREE LOOP #39 Winter Springs, FL Welcome to your move-in ready 3-bedroom, 2.5-bath townhome-style condo located in the desi...	3 beds \| 3 baths \| 1,400 sq.ft.	$210,000	Airbnb cash on cash: 8.67% Traditional cash on cash: 5.37% Airbnb Rental Income: $3583 Traditional Rental Income: $2141 Airbnb ROI: 8.67% Traditional ROI: 5.37%
998 EL LAGO TERRACE Winter Springs, FL PAID-OFF SOLAR! Welcome to Sunrise Estates and your opportunity to own a truly unique prop...	4 beds \| 2 baths \| 2,126 sq.ft.	$649,900	Airbnb cash on cash: 2.78% Traditional cash on cash: 4.08% Airbnb Rental Income: $3298 Traditional Rental Income: $3342 Airbnb ROI: 2.78% Traditional ROI: 4.08%
1360 VIA VILLA NOVA WAY Winter Springs, FL Location, Location, Location... Don't miss out this opportunity to own a turn-key home in ...	4 beds \| 2 baths \| 2,064 sq.ft.	$539,999	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.09% Airbnb Rental Income: $3298 Traditional Rental Income: $2955 Airbnb ROI: 3.3% Traditional ROI: 4.09%
934 TORREY PINE DRIVE Winter Springs, FL Virtually Staged. Beautifully remodeled golf course home in the highly desirable Tuscawill...	3 beds \| 2 baths \| 1,678 sq.ft.	$499,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.89% Airbnb Rental Income: $3583 Traditional Rental Income: $2726 Airbnb ROI: 4.04% Traditional ROI: 3.89%
314 SAN GABRIEL STREET Winter Springs, FL **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE ...	3 beds \| 2 baths \| 1,091 sq.ft.	$279,990	Airbnb cash on cash: 7.93% Traditional cash on cash: 5.5% Airbnb Rental Income: $3583 Traditional Rental Income: $2157 Airbnb ROI: 7.93% Traditional ROI: 5.5%
270 SAN GABRIEL STREET Winter Springs, FL Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springsânow offered...	3 beds \| 2 baths \| 1,089 sq.ft.	$249,900	Airbnb cash on cash: 9.75% Traditional cash on cash: 7.55% Airbnb Rental Income: $3583 Traditional Rental Income: $2278 Airbnb ROI: 9.75% Traditional ROI: 7.55%
114 SUNDANCE COURT Winter Springs, FL One or more photo(s) has been virtually staged. If youâve been searching for space, loca...	4 beds \| 2 baths \| 1,356 sq.ft.	$305,500	Airbnb cash on cash: 5.8% Traditional cash on cash: 5.95% Airbnb Rental Income: $3298 Traditional Rental Income: $2602 Airbnb ROI: 5.8% Traditional ROI: 5.95%
506 CLUB DRIVE Winter Springs, FL Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! ...	2 beds \| 2 baths \| 1,002 sq.ft.	$232,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 4.41% Airbnb Rental Income: $960 Traditional Rental Income: $1900 Airbnb ROI: -1.47% Traditional ROI: 4.41%
124 BLUE CREEK DRIVE Winter Springs, FL Welcome to this 5 bedroom, 3 bathroom pool home in the highly desirable Tuskawilla neighbo...	5 beds \| 3 baths \| 2,762 sq.ft.	$725,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.97% Airbnb Rental Income: $5023 Traditional Rental Income: $4314 Airbnb ROI: 3.5% Traditional ROI: 3.97%
1815 SENECA BOULEVARD Winter Springs, FL Welcome to this beautifully reimagined 5-bedroom, 3 full bath, 2 half bath pool home locat...	5 beds \| 5 baths \| 3,885 sq.ft.	$998,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.16% Airbnb Rental Income: $5023 Traditional Rental Income: $5397 Airbnb ROI: 2.65% Traditional ROI: 4.16%
986 TURKEY HOLLOW CIRCLE Winter Springs, FL 986 Turkey Hollow Circleâwhere comfort, style, and Florida living come together beautifu...	4 beds \| 2 baths \| 1,864 sq.ft.	$494,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.94% Airbnb Rental Income: $3298 Traditional Rental Income: $3130 Airbnb ROI: 3.7% Traditional ROI: 4.94%
632 BLENHEIM LOOP Winter Springs, FL Good afternoon and welcome to your new 4 bedroom, 3 bathroom, and 2 car garage gated commu...	4 beds \| 3 baths \| 1,996 sq.ft.	$489,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 4.31% Airbnb Rental Income: $3298 Traditional Rental Income: $2946 Airbnb ROI: 3.47% Traditional ROI: 4.31%
116 PHILADELPHIA WAY Winter Springs, FL Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated community, offering a grea...	3 beds \| 3 baths \| 1,468 sq.ft.	$310,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 4.53% Airbnb Rental Income: $3583 Traditional Rental Income: $2430 Airbnb ROI: 5.79% Traditional ROI: 4.53%
101 PARTRIDGE CIRCLE Winter Springs, FL Under contract-accepting backup offers. Situated on a spacious 0.38-acre lot in the highly...	3 beds \| 2 baths \| 2,181 sq.ft.	$625,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 3.4% Airbnb Rental Income: $3583 Traditional Rental Income: $2907 Airbnb ROI: 3.22% Traditional ROI: 3.4%
30 SABLE COURT Winter Springs, FL REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community...	4 beds \| 3 baths \| 2,674 sq.ft.	$569,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 6% Airbnb Rental Income: $3298 Traditional Rental Income: $4099 Airbnb ROI: 3.11% Traditional ROI: 6%
214 CHESTNUT RIDGE STREET Winter Springs, FL Under contract-accepting backup offers. WOW, BEST PRICE IN Winter Springs! Executive TUSCA...	4 beds \| 3 baths \| 2,474 sq.ft.	$590,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.79% Airbnb Rental Income: $3298 Traditional Rental Income: $3292 Airbnb ROI: 2.46% Traditional ROI: 3.79%
167 CONSTITUTION WAY Winter Springs, FL Welcome to easy, low maintenance living in the gated Heritage Park community of Winter Spr...	2 beds \| 3 baths \| 1,275 sq.ft.	$294,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 4.55% Airbnb Rental Income: $960 Traditional Rental Income: $2202 Airbnb ROI: -1.2% Traditional ROI: 4.55%

Real Estate investment in Winter-springs, FL

There are 115 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $441,736 and the average price per square foot is $225. In July 2026, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,471.

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

There are 115 investment properties available for sale in Winter-springs.

In 2026, the best neighborhood to buy investment property is Winter Springs.

The ROI for Short-Term is higher than the Long-Term in Winter-springs with average rental income of $3,583.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Springs, FL

710 BRIARWOOD DRIVE

Winter Springs, FL

4 beds | 2 baths | 1,769 sq.ft.

$360,000

Airbnb cash on cash: 4.88%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $3298

Traditional Rental Income: $2724

Airbnb ROI: 4.88%

Traditional ROI: 5.37%

440 BUCKSKIN COURT

Winter Springs, FL

4 beds | 3 baths | 1,922 sq.ft.

$525,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $3298

Traditional Rental Income: $2804

Airbnb ROI: 2.87%

Traditional ROI: 3.37%

451 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,914 sq.ft.

$357,500

Airbnb cash on cash: 5.01%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3583

Traditional Rental Income: $2637

Airbnb ROI: 5.01%

Traditional ROI: 4.53%

471 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,680 sq.ft.

$330,000

Airbnb cash on cash: 5.28%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $3583

Traditional Rental Income: $2627

Airbnb ROI: 5.28%

Traditional ROI: 4.74%

131 LISA LOOP

Winter Springs, FL

4 beds | 3 baths | 2,309 sq.ft.

$489,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $3298

Traditional Rental Income: $3167

Airbnb ROI: 3.07%

Traditional ROI: 4.39%

1201 WOLVERINE TRAIL

Winter Springs, FL

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

$500,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $3298

Traditional Rental Income: $2930

Airbnb ROI: 3.14%

Traditional ROI: 3.93%

1024 DINERO DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,463 sq.ft.

$419,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $3583

Traditional Rental Income: $2341

Airbnb ROI: 4.65%

Traditional ROI: 3.49%

299 WOODGREEN LANE

Winter Springs, FL

3 beds | 3 baths | 1,326 sq.ft.

$285,000

Airbnb cash on cash: 7.56%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $3583

Traditional Rental Income: $1876

Airbnb ROI: 7.56%