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
600 NORTHERN WAY #806 Winter Springs, FL Welcome to your new home in the Winter Springâs community of Tuscany Place where you wil...	3 beds \| 3 baths \| 1,447 sq.ft.	$305,000	Airbnb cash on cash: 8.83% Traditional cash on cash: 5.08% Airbnb Rental Income: $4244 Traditional Rental Income: $2269 Airbnb ROI: 8.83% Traditional ROI: 5.08%
1392 CONGRESSIONAL COURT Winter Springs, FL Welcome to this luxurious 2-story townhome in the highly-desired, gated community of The G...	2 beds \| 3 baths \| 1,740 sq.ft.	$475,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.57% Airbnb Rental Income: $3122 Traditional Rental Income: $2115 Airbnb ROI: 2.24% Traditional ROI: 1.57%
600 NORTHERN WAY #609 Winter Springs, FL Under contract-accepting backup offers. This three bedroom, three bath townhome style cond...	3 beds \| 3 baths \| 1,447 sq.ft.	$315,000	Airbnb cash on cash: 9.05% Traditional cash on cash: 5.16% Airbnb Rental Income: $4244 Traditional Rental Income: $2193 Airbnb ROI: 9.05% Traditional ROI: 5.16%
535 CRIMSON LANE Winter Springs, FL Welcome to 535 Crimson Ln in the charming community of Jesups Reserve in Winter Springs! T...	3 beds \| 4 baths \| 1,872 sq.ft.	$400,000	Airbnb cash on cash: 6.24% Traditional cash on cash: 4.8% Airbnb Rental Income: $4244 Traditional Rental Income: $2809 Airbnb ROI: 6.24% Traditional ROI: 4.8%
1705 GALWAY COURT Winter Springs, FL Under contract-accepting backup offers. Welcome to your Winter Springs dream home, located...	4 beds \| 2 baths \| 2,449 sq.ft.	$634,900	Airbnb cash on cash: 4.55% Traditional cash on cash: 3.32% Airbnb Rental Income: $4777 Traditional Rental Income: $3062 Airbnb ROI: 4.55% Traditional ROI: 3.32%
4048 W DANBY COURT Winter Springs, FL MOTIVATED SELLER-RELOCATING! Outstanding opportunity in the market! This expansive, recent...	5 beds \| 4 baths \| 4,087 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $4400 Airbnb ROI: N/A Traditional ROI: 3.36%
1157 ORANGE AVENUE Winter Springs, FL This stunning 3-bedroom, 3.5-bathroom townhome offers spacious living across three levels ...	3 beds \| 4 baths \| 2,104 sq.ft.	$420,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 5.27% Airbnb Rental Income: $4244 Traditional Rental Income: $3034 Airbnb ROI: 6.07% Traditional ROI: 5.27%
967 WEDGEWOOD DRIVE Winter Springs, FL Your POOL HOME ON THE GOLF COURSE is Ready! Don't wait, come over, walk through it; this i...	3 beds \| 2 baths \| 1,472 sq.ft.	$449,000	Airbnb cash on cash: 5.91% Traditional cash on cash: 3.53% Airbnb Rental Income: $4244 Traditional Rental Income: $2347 Airbnb ROI: 5.91% Traditional ROI: 3.53%
1106 ERMINE AVENUE Winter Springs, FL Under contract-accepting backup offers. Need a spacious pool home? Look no further .This 4...	4 beds \| 2 baths \| 2,050 sq.ft.	$475,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 4% Airbnb Rental Income: $4777 Traditional Rental Income: $2882 Airbnb ROI: 6.05% Traditional ROI: 4%
1229 WINDING CHASE BOULEVARD Winter Springs, FL Discover your dream home in the heart of a desirable community of WINDING HOLLOW! This stu...	5 beds \| 3 baths \| 2,501 sq.ft.	$630,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $3430 Airbnb ROI: N/A Traditional ROI: 3.52%
782 SENECA MEADOWS ROAD Winter Springs, FL Welcome Home to Your Dream Pool Oasis in the Gated Community of Parkstone! Nestled in t...	4 beds \| 2 baths \| 1,947 sq.ft.	$499,900	Airbnb cash on cash: 5.92% Traditional cash on cash: 3.56% Airbnb Rental Income: $4777 Traditional Rental Income: $2688 Airbnb ROI: 5.92% Traditional ROI: 3.56%
252 TAVESTOCK LOOP Winter Springs, FL Welcome to Your Dream Home in Parkstone! Discover this beautifully updated 4-bedroom, 3.5...	4 beds \| 4 baths \| 2,888 sq.ft.	$655,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 3.52% Airbnb Rental Income: $4777 Traditional Rental Income: $3581 Airbnb ROI: 3.86% Traditional ROI: 3.52%
229 SHERRY AVENUE Winter Springs, FL Welcome to this 3-bedroom, 1-bathroom home in the heart of Winter Springs! Situated in a p...	3 beds \| 1 baths \| 1,104 sq.ft.	$310,000	Airbnb cash on cash: 8.89% Traditional cash on cash: 3.05% Airbnb Rental Income: $4244 Traditional Rental Income: $1645 Airbnb ROI: 8.89% Traditional ROI: 3.05%
1254 ROYAL OAK DRIVE Winter Springs, FL Don't miss this stunning home backing up to the golf course in the sought after Tuscawilla...	3 beds \| 3 baths \| 2,110 sq.ft.	$574,900	Airbnb cash on cash: 4.17% Traditional cash on cash: 3.61% Airbnb Rental Income: $4244 Traditional Rental Income: $3047 Airbnb ROI: 4.17% Traditional ROI: 3.61%
721 SAILFISH ROAD Winter Springs, FL Beautiful 3 bedroom 2 full bathroom POOL HOME on conservation lot in gorgeous North Orland...	3 beds \| 2 baths \| 1,378 sq.ft.	$399,900	Airbnb cash on cash: 6.66% Traditional cash on cash: 3.56% Airbnb Rental Income: $4244 Traditional Rental Income: $2185 Airbnb ROI: 6.66% Traditional ROI: 3.56%
608 ALTON ROAD Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this inviting 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,304 sq.ft.	$400,000	Airbnb cash on cash: 7.4% Traditional cash on cash: 3.83% Airbnb Rental Income: $4244 Traditional Rental Income: $2008 Airbnb ROI: 7.4% Traditional ROI: 3.83%
206 MORTON LANE Winter Springs, FL Discover the epitome of LAKESIDE LIVING in this stunning 4-bedroom, 2.5-bathroom home nest...	4 beds \| 3 baths \| 2,916 sq.ft.	$815,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.16% Airbnb Rental Income: $4777 Traditional Rental Income: $3089 Airbnb ROI: 3.08% Traditional ROI: 2.16%
1560 EAGLE NEST CIRCLE Winter Springs, FL 4 Bedroom, 3 bathroom custom home in desirable Glen Eagle of Tuscawilla! From the attracti...	4 beds \| 3 baths \| 2,894 sq.ft.	$799,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 2.38% Airbnb Rental Income: $4777 Traditional Rental Income: $3505 Airbnb ROI: 2.77% Traditional ROI: 2.38%
384 INNISBROOK LANE Winter Springs, FL Welcome to Your Dream Home in Winter Springs! This stunning, modern 3-story townhouse is t...	3 beds \| 4 baths \| 1,844 sq.ft.	$389,900	Airbnb cash on cash: 5.84% Traditional cash on cash: 4.39% Airbnb Rental Income: $4244 Traditional Rental Income: $2819 Airbnb ROI: 5.84% Traditional ROI: 4.39%
3932 WHITE BIRCH RUN Winter Springs, FL Welcome to 3932 White Birch Run, a beautifully maintained end-unit townhome located in the...	4 beds \| 3 baths \| 1,960 sq.ft.	$375,000	Airbnb cash on cash: 7.46% Traditional cash on cash: 4.09% Airbnb Rental Income: $4777 Traditional Rental Income: $2604 Airbnb ROI: 7.46% Traditional ROI: 4.09%
502 OSPREY LANE Winter Springs, FL *** Price reduction of $15,500 and seller is offering $10,000 in concessions toward closin...	3 beds \| 2 baths \| 1,708 sq.ft.	$394,500	Airbnb cash on cash: 6.66% Traditional cash on cash: 3.77% Airbnb Rental Income: $4244 Traditional Rental Income: $2279 Airbnb ROI: 6.66% Traditional ROI: 3.77%
537 SHADOW GLENN PLACE Winter Springs, FL Come take a look at this lovely property in beautiful Winter Springs, Florida. Lovingly up...	3 beds \| 3 baths \| 1,359 sq.ft.	$307,700	Airbnb cash on cash: 7.26% Traditional cash on cash: 2.31% Airbnb Rental Income: $4244 Traditional Rental Income: $1912 Airbnb ROI: 7.26% Traditional ROI: 2.31%
1474 WHITEHALL BOULEVARD Winter Springs, FL Under contract-accepting backup offers. Discover the perfect blend of charm and modern upd...	3 beds \| 2 baths \| 1,628 sq.ft.	$450,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 2.55% Airbnb Rental Income: $4244 Traditional Rental Income: $2189 Airbnb ROI: 5.3% Traditional ROI: 2.55%
1517 EAGLE NEST CIRCLE Winter Springs, FL Under contract-accepting backup offers. IMPRESSIVE MODERNIZED MASTERPIECE IN GLEN EAGLE! T...	4 beds \| 3 baths \| 2,685 sq.ft.	$800,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 2.39% Airbnb Rental Income: $4777 Traditional Rental Income: $3413 Airbnb ROI: 2.9% Traditional ROI: 2.39%
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.	$325,000	Airbnb cash on cash: 8.46% Traditional cash on cash: 4.19% Airbnb Rental Income: $4244 Traditional Rental Income: $2045 Airbnb ROI: 8.46% Traditional ROI: 4.19%
918 TORREY PINE DRIVE Winter Springs, FL Under contract-accepting backup offers. Come see this Beautiful Mediterranean Style Home o...	3 beds \| 2 baths \| 2,019 sq.ft.	$515,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 2.51% Airbnb Rental Income: $4244 Traditional Rental Income: $2455 Airbnb ROI: 4.37% Traditional ROI: 2.51%
707 SUNBURY DRIVE Winter Springs, FL **This property qualifies for a closing cost credit up to $2,700 through the Sellerâs pr...	3 beds \| 2 baths \| 1,328 sq.ft.	$360,000	Airbnb cash on cash: 7.28% Traditional cash on cash: 5.96% Airbnb Rental Income: $4244 Traditional Rental Income: $2902 Airbnb ROI: 7.28% Traditional ROI: 5.96%
1314 Augusta National Blvd Winter Springs, FL	3 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 2.64% Airbnb Rental Income: $4244 Traditional Rental Income: $2626 Airbnb ROI: 3.93% Traditional ROI: 2.64%
1314 Augusta National Blvd Winter Springs, FL	3 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 2.64% Airbnb Rental Income: $4244 Traditional Rental Income: $2626 Airbnb ROI: 3.93% Traditional ROI: 2.64%
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: 3.73% Traditional cash on cash: 2.23% Airbnb Rental Income: $4244 Traditional Rental Income: $2508 Airbnb ROI: 3.73% Traditional ROI: 2.23%
727 ADIDAS ROAD Winter Springs, FL Under contract-accepting backup offers. Discover your next home at 727 Adidas Rd, Winter S...	2 beds \| 2 baths \| 1,570 sq.ft.	$399,999	Airbnb cash on cash: 3.86% Traditional cash on cash: 3.89% Airbnb Rental Income: $3122 Traditional Rental Income: $2424 Airbnb ROI: 3.86% Traditional ROI: 3.89%
521 CRUZ BAY CIRCLE Winter Springs, FL Under contract-accepting backup offers. Welcome to this move-in ready three-bedroom, two-a...	3 beds \| 3 baths \| 1,914 sq.ft.	$409,900	Airbnb cash on cash: 5.69% Traditional cash on cash: 2.94% Airbnb Rental Income: $4244 Traditional Rental Income: $2293 Airbnb ROI: 5.69% Traditional ROI: 2.94%
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.	$589,900	Airbnb cash on cash: 4.14% Traditional cash on cash: 4.41% Airbnb Rental Income: $4777 Traditional Rental Income: $3942 Airbnb ROI: 4.14% Traditional ROI: 4.41%
31 S EDGEMON AVENUE Winter Springs, FL This charming home offers a spacious floor plan with a unique twistâ the garage has been...	3 beds \| 2 baths \| 1,270 sq.ft.	$386,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 3.67% Airbnb Rental Income: $4244 Traditional Rental Income: $2038 Airbnb ROI: 7.29% Traditional ROI: 3.67%
237 MOCKINGBIRD LANE Winter Springs, FL Under contract-accepting backup offers. Welcome to your new home! This beautifully maintai...	4 beds \| 2 baths \| 2,502 sq.ft.	$459,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 5.4% Airbnb Rental Income: $4777 Traditional Rental Income: $3051 Airbnb ROI: 7.12% Traditional ROI: 5.4%
377 TWELVE OAKS DRIVE Winter Springs, FL This stunning 4-bedroom home (2,157 sq ft) in Winter Springs' Winding Hollow neighborhood ...	4 beds \| 3 baths \| 2,157 sq.ft.	$545,000	Airbnb cash on cash: 5.53% Traditional cash on cash: 3.89% Airbnb Rental Income: $4777 Traditional Rental Income: $2958 Airbnb ROI: 5.53% Traditional ROI: 3.89%
450 TRADITION LANE Winter Springs, FL Welcome to your TURNKEY dream home in the desirable Heritage Park Community. This move-in ...	3 beds \| 3 baths \| 1,468 sq.ft.	$355,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 3.1% Airbnb Rental Income: $4244 Traditional Rental Income: $2099 Airbnb ROI: 6.85% Traditional ROI: 3.1%
530 JULIE LANE Winter Springs, FL Rare opportunity in sought after Dunmar Estates. Tucked away on 6.43 acres of beautiful l...	4 beds \| 4 baths \| 3,195 sq.ft.	$1,400,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.28% Airbnb Rental Income: $4777 Traditional Rental Income: $4258 Airbnb ROI: 0.92% Traditional ROI: 1.28%
1101 MARCUS COURT Winter Springs, FL One or more photo(s) has been virtually staged.Seller may consider buyer concessions if ma...	4 beds \| 3 baths \| 2,540 sq.ft.	$675,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.08% Airbnb Rental Income: $4777 Traditional Rental Income: $3329 Airbnb ROI: 3.82% Traditional ROI: 3.08%
1209 GEMA PLACE Winter Springs, FL Renovated Open floor plan with 2-sided wood burning fireplace, vaulted ceilings, open ligh...	3 beds \| 2 baths \| 1,731 sq.ft.	$449,995	Airbnb cash on cash: 5.67% Traditional cash on cash: 3.22% Airbnb Rental Income: $4244 Traditional Rental Income: $2316 Airbnb ROI: 5.67% Traditional ROI: 3.22%

Real Estate investment in Winter-springs, FL

There are 102 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $435,750 and the average price per square foot is $217. In December 2024, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,499.

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

There are 102 investment properties available for sale in Winter-springs.

The ROI for Short-Term is higher than the Long-Term in Winter-springs with average rental income of $4,244.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Springs, FL

600 NORTHERN WAY #806

Winter Springs, FL

3 beds | 3 baths | 1,447 sq.ft.

$305,000

Airbnb cash on cash: 8.83%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $4244

Traditional Rental Income: $2269

Airbnb ROI: 8.83%

Traditional ROI: 5.08%

1392 CONGRESSIONAL COURT

Winter Springs, FL

2 beds | 3 baths | 1,740 sq.ft.

$475,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 1.57%

Airbnb Rental Income: $3122

Traditional Rental Income: $2115

Airbnb ROI: 2.24%

Traditional ROI: 1.57%

600 NORTHERN WAY #609

Winter Springs, FL

3 beds | 3 baths | 1,447 sq.ft.

$315,000

Airbnb cash on cash: 9.05%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $4244

Traditional Rental Income: $2193

Airbnb ROI: 9.05%

Traditional ROI: 5.16%

535 CRIMSON LANE

Winter Springs, FL

3 beds | 4 baths | 1,872 sq.ft.

$400,000

Airbnb cash on cash: 6.24%

Traditional cash on cash: 4.8%

Airbnb Rental Income: $4244

Traditional Rental Income: $2809

Airbnb ROI: 6.24%

Traditional ROI: 4.8%

1705 GALWAY COURT

Winter Springs, FL

4 beds | 2 baths | 2,449 sq.ft.

$634,900

Airbnb cash on cash: 4.55%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $4777

Traditional Rental Income: $3062

Airbnb ROI: 4.55%

Traditional ROI: 3.32%

4048 W DANBY COURT

Winter Springs, FL

5 beds | 4 baths | 4,087 sq.ft.

$899,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.36%

Airbnb Rental Income: $null

Traditional Rental Income: $4400

Airbnb ROI: N/A

Traditional ROI: 3.36%

1157 ORANGE AVENUE

Winter Springs, FL

3 beds | 4 baths | 2,104 sq.ft.

$420,000

Airbnb cash on cash: 6.07%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $4244

Traditional Rental Income: $3034

Airbnb ROI: 6.07%

Traditional ROI: 5.27%

967 WEDGEWOOD DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,472 sq.ft.

$449,000

Airbnb cash on cash: 5.91%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $4244

Traditional Rental Income: $2347

Airbnb ROI: 5.91%