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 80 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
116 Avery Lake Dr Winter Springs, FL Welcome to this beautifully upgraded 4-bedroom, 2-bathroom home in Avery Park, where moder...	4 beds \| 2 baths \| 2,714 sq.ft.	$629,999	Airbnb cash on cash: 5.04% Traditional cash on cash: 2.45% Airbnb Rental Income: $5258 Traditional Rental Income: $2669 Airbnb ROI: 5.04% Traditional ROI: 2.45%
710 BRIARWOOD Drive Winter Springs, FL Virtually Staged. MOVE-IN READY WITH BRAND-NEW HVAC SYSTEM! Welcome to this beautifully up...	4 beds \| 2 baths \| 1,769 sq.ft.	$355,000	Airbnb cash on cash: 9.86% Traditional cash on cash: 5.46% Airbnb Rental Income: $5258 Traditional Rental Income: $2724 Airbnb ROI: 9.86% Traditional ROI: 5.46%
1162 E Winged Foot Cir Winter Springs, FL Welcome to this beautifully maintained 3-bedroom, 2-bath POOL home nestled on a quiet, tre...	3 beds \| 2 baths \| 1,574 sq.ft.	$425,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 2.83% Airbnb Rental Income: $3773 Traditional Rental Income: $2386 Airbnb ROI: 4.21% Traditional ROI: 2.83%
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.	$490,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 4.03% Airbnb Rental Income: $5258 Traditional Rental Income: $2930 Airbnb ROI: 6.79% Traditional ROI: 4.03%
758 N Gretna Ct Winter Springs, FL Welcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both...	4 beds \| 3 baths \| 2,150 sq.ft.	$390,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 5.11% Airbnb Rental Income: $5258 Traditional Rental Income: $2892 Airbnb ROI: 8.58% Traditional ROI: 5.11%
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.	$394,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 3.77% Airbnb Rental Income: $3773 Traditional Rental Income: $2341 Airbnb ROI: 5.43% Traditional ROI: 3.77%
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: 1.17% Traditional cash on cash: 2.23% Airbnb Rental Income: $2523 Traditional Rental Income: $2508 Airbnb ROI: 1.17% Traditional ROI: 2.23%
212 S Cortez Ave Winter Springs, FL POOL HOME WITH PRIVATE IN-LAW SUITE! Welcome to this beautifully updated 4-bedroom, 3-bath...	4 beds \| 3 baths \| 1,344 sq.ft.	$375,000	Airbnb cash on cash: 9.31% Traditional cash on cash: 7.13% Airbnb Rental Income: $5258 Traditional Rental Income: $3428 Airbnb ROI: 9.31% Traditional ROI: 7.13%
276 SAN GABRIEL Street Winter Springs, FL Priced to Sell! This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity f...	3 beds \| 2 baths \| 1,089 sq.ft.	$278,900	Airbnb cash on cash: 8.03% Traditional cash on cash: 4.39% Airbnb Rental Income: $3773 Traditional Rental Income: $1998 Airbnb ROI: 8.03% Traditional ROI: 4.39%
142 Bayberry Ct Winter Springs, FL PRICE IMPROVEMENT: This 4 bedroom 2 bath home located on a quiet cul de sac is perfect for...	4 beds \| 2 baths \| 1,425 sq.ft.	$359,000	Airbnb cash on cash: 9.76% Traditional cash on cash: 4.1% Airbnb Rental Income: $5258 Traditional Rental Income: $2254 Airbnb ROI: 9.76% Traditional ROI: 4.1%
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.	$755,000	Airbnb cash on cash: 7.16% Traditional cash on cash: 3.36% Airbnb Rental Income: $8126 Traditional Rental Income: $3908 Airbnb ROI: 7.16% Traditional ROI: 3.36%
717 LANCEWOOD Drive Winter Springs, FL MOVE-IN READY HOME on an amazing 0.3-acre corner lot! In the heart of Seminole County's Wi...	3 beds \| 2 baths \| 1,616 sq.ft.	$359,900	Airbnb cash on cash: 7.1% Traditional cash on cash: 5.9% Airbnb Rental Income: $3773 Traditional Rental Income: $2549 Airbnb ROI: 7.1% Traditional ROI: 5.9%
717 Adidas Rd Winter Springs, FL Virtually Staged. Welcome home to this absolutely charming and move-in-ready 2-bedroom, 2-...	2 beds \| 2 baths \| 1,812 sq.ft.	$414,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 4.16% Airbnb Rental Income: $1247 Traditional Rental Income: $2770 Airbnb ROI: -0.72% Traditional ROI: 4.16%
632 Blenheim Loop Winter Springs, FL JUST REDUCED, This home is updated, renovated, well maintained in a beautiful and a family...	4 beds \| 2 baths \| 1,996 sq.ft.	$484,900	Airbnb cash on cash: 7.11% Traditional cash on cash: 4.37% Airbnb Rental Income: $5258 Traditional Rental Income: $2946 Airbnb ROI: 7.11% Traditional ROI: 4.37%
120 E BAHAMA Road Winter Springs, FL Mid-Century Modern Paradise!! A Beautiful, well-designed home with spectacular architectur...	4 beds \| 3 baths \| 4,464 sq.ft.	$959,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 2.5% Airbnb Rental Income: $5258 Traditional Rental Income: $4373 Airbnb ROI: 2.3% Traditional ROI: 2.5%
30 Sable Ct Winter Springs, FL Under contract-accepting backup offers. REDUCED! Beautiful Executive 4 bedroom POOL home i...	4 beds \| 2 baths \| 2,674 sq.ft.	$539,900	Airbnb cash on cash: 6.56% Traditional cash on cash: 6.38% Airbnb Rental Income: $5258 Traditional Rental Income: $4099 Airbnb ROI: 6.56% Traditional ROI: 6.38%
421 Horizon Dr Winter Springs, FL MOTIVATED SELLERS!!! Welcome to 421 Horizon Drive in Winter Springs, located in The Season...	3 beds \| 2 baths \| 1,069 sq.ft.	$285,000	Airbnb cash on cash: 7.79% Traditional cash on cash: 5% Airbnb Rental Income: $3773 Traditional Rental Income: $2205 Airbnb ROI: 7.79% Traditional ROI: 5%
130 Deer Song Dr Winter Springs, FL Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to o...	3 beds \| 2 baths \| 1,105 sq.ft.	$310,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 5.17% Airbnb Rental Income: $3773 Traditional Rental Income: $2323 Airbnb ROI: 7.34% Traditional ROI: 5.17%
156 Seville Chase Dr Winter Springs, FL Virtually Staged. AMAZING OPPORTUNITY: THIS IS THE LOWEST PRICED HOME IN THIS COMMUNITY! W...	4 beds \| 3 baths \| 2,509 sq.ft.	$649,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.29% Airbnb Rental Income: $5258 Traditional Rental Income: $3165 Airbnb ROI: 4.99% Traditional ROI: 3.29%
4910 E Lake Dr Winter Springs, FL A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complet...	3 beds \| 3 baths \| 3,657 sq.ft.	$2,299,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.17% Airbnb Rental Income: $3773 Traditional Rental Income: $3279 Airbnb ROI: 0.03% Traditional ROI: 0.17%
335 Kirkcaldy Dr Winter Springs, FL Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like...	3 beds \| 2 baths \| 1,178 sq.ft.	$324,900	Airbnb cash on cash: 6.97% Traditional cash on cash: 3.86% Airbnb Rental Income: $3773 Traditional Rental Income: $1991 Airbnb ROI: 6.97% Traditional ROI: 3.86%
268 Tavestock Loop Winter Springs, FL New Price 268 Tavestock Loop, Winter Springs, FL 32708 Perfectly situated in the heart...	4 beds \| 2 baths \| 2,415 sq.ft.	$557,900	Airbnb cash on cash: 5.78% Traditional cash on cash: 3.36% Airbnb Rental Income: $5258 Traditional Rental Income: $2933 Airbnb ROI: 5.78% Traditional ROI: 3.36%
339 INGLENOOK Circle Winter Springs, FL Under contract-accepting backup offers. ACCEPTING BACK-UP OFFERS! New Roof Being Installed...	3 beds \| 2 baths \| 1,437 sq.ft.	$359,900	Airbnb cash on cash: 6.07% Traditional cash on cash: 3.77% Airbnb Rental Income: $3773 Traditional Rental Income: $2177 Airbnb ROI: 6.07% Traditional ROI: 3.77%
114 STONE GABLE Circle Winter Springs, FL Welcome to the desirable city of Winter Springs, where 114 Stone Gable Cir sits on a beaut...	3 beds \| 2 baths \| 1,814 sq.ft.	$479,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 4.35% Airbnb Rental Income: $3773 Traditional Rental Income: $2941 Airbnb ROI: 4.38% Traditional ROI: 4.35%
170 WOODED VINE Drive Winter Springs, FL Built in 2019, this thoughtfully designed floor plan is ideal for multigenerational living...	4 beds \| 4 baths \| 2,470 sq.ft.	$620,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 2.92% Airbnb Rental Income: $5258 Traditional Rental Income: $3306 Airbnb ROI: 4.45% Traditional ROI: 2.92%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winter Springs, FL

116 Avery Lake Dr

Winter Springs, FL

4 beds | 2 baths | 2,714 sq.ft.

$629,999

Airbnb cash on cash: 5.04%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $5258

Traditional Rental Income: $2669

Airbnb ROI: 5.04%

Traditional ROI: 2.45%

710 BRIARWOOD Drive

Winter Springs, FL

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

$355,000

Airbnb cash on cash: 9.86%

Traditional cash on cash: 5.46%

Airbnb Rental Income: $5258

Traditional Rental Income: $2724

Airbnb ROI: 9.86%

Traditional ROI: 5.46%

1162 E Winged Foot Cir

Winter Springs, FL

3 beds | 2 baths | 1,574 sq.ft.

$425,000

Airbnb cash on cash: 4.21%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $3773

Traditional Rental Income: $2386

Airbnb ROI: 4.21%

Traditional ROI: 2.83%

1201 WOLVERINE Trail

Winter Springs, FL

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

$490,000

Airbnb cash on cash: 6.79%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $5258

Traditional Rental Income: $2930

Airbnb ROI: 6.79%

Traditional ROI: 4.03%

758 N Gretna Ct

Winter Springs, FL

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

$390,000

Airbnb cash on cash: 8.58%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $5258

Traditional Rental Income: $2892

Airbnb ROI: 8.58%

Traditional ROI: 5.11%

1024 DINERO Drive

Winter Springs, FL

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

$394,000

Airbnb cash on cash: 5.43%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $3773

Traditional Rental Income: $2341

Airbnb ROI: 5.43%

Traditional ROI: 3.77%

1314 Augusta National Blvd

Winter Springs, FL

3 beds | 3 baths | 2,004 sq.ft.

$600,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $2523

Traditional Rental Income: $2508

Airbnb ROI: 1.17%

Traditional ROI: 2.23%

212 S Cortez Ave

Winter Springs, FL

4 beds | 3 baths | 1,344 sq.ft.

$375,000

Airbnb cash on cash: 9.31%

Traditional cash on cash: 7.13%

Airbnb Rental Income: $5258

Traditional Rental Income: $3428

Airbnb ROI: 9.31%